On April 22, 2021, Boyle, Robert George; Walker, David Winter; Major, Meriel Ruth published a patent.Computed Properties of 357935-97-8 The title of the patent was Preparation of pyrrolo[2,3-d]pyrimidine derivatives and their use in the treatment of cancer. And the patent contained the following:
The title compounds I [A = CH or N; R1 = C(OH)(Alk1)(Alk2), N:S(O)(Alk3)(Alk4), or Q; Alk1, Alk2 = same or different C1-3 saturated hydrocarbyl; or Alk1 and Alk2 together with the carbon atom to which they are attached form a C3-4 cycloalkyl ring; Alk3, Alk4 = same or different C1-3 hydrocarbyl; or Alk3 and Alk4 together with the sulfur atom to which they are attached form a 4-6 membered thiacycloalkyl ring; p = 1,2; q = 1,2, provided that the sum of p + q is either 2 or 3; R8 = H, F or Me; R2 = H, halo, C1-3 alkyl C1-3 alkoxy, or C1-3 fluoroalkyl; R3 = H, F, or Me; R4 = H, F, Me, or cyano; R5 = L-Cyc1; L = (CH2)m-B-(CH2)n; m, n = independently 0 or 1; B = absent or C(O)N(Rc), N(Rc)C(O), N(Rc), O, N(Rc)CH2C(O), S, S(O), or S(O)2; Rc = H or C1-4 hydrocarbyl; Cyc1 = each (un)substituted C3-6 cycloalkyl, 4- to 7-membered monocyclic or heterocyclic group containing 1 or 2 heteroatoms selected from N and O, 7- to 11-membered bicyclic heterocyclic group containing 1 or 2 heteroatoms selected from N and O, or phenyl; R6 = H, halo, C1-4 alkyl, C1-4 alkoxy, or C1-4 fluoroalkyl; R7 = C1-4 hydrocarbyl, halo, hydroxy, oxo, C(O)Ra, C(O)ORa, C(O)N(Ra)(Rb), N(Rb)C(O)Ra, N(Rb)C(O)N(Ra)(Rb), or C2-5alkane-diyl, wherein the C2-5alkane-diyl group together with an atom or atoms of Cyc1 to which it is attached forms a cyclic group; Ra, Rb = independently H or C1-3 hydrocarbyl] are prepared The compounds I also including or salts or tautomers thereof are inhibitors of Wee1 kinase and/or PLK1 kinase and are envisaged to be useful in the treatment of cancers. Thus, 2-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine was coupled with 2-(6-bromo-2-pyridyl)propanol in the presence of CuI, trans-N,N’-dimethylcyclohexane, and K3PO4 in 1,4-dioxane at 100° for 12 h under nitrogen to give 98% 2-[6-(2-chloro-5-fluoropyrrolo[2,3-d]pyrimidin-7-yl)-2-pyridyl]propan-2-ol which was coupled with tert-Bu 4-(4-aminophenyl)piperazine-1-carboxylate in the presence of Li-HMDS in THF at 0° for 30 min and at 100° for 2 h to give 40% tert-Bu 4-[4-[[5-fluoro-7-[6-(1-hydroxy-1-methylethyl)-2-pyridyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazine-1-carboxylate (II; R = Boc). II (R = Boc) was treated with 4 N HCl/1,4-dioxane at room temperature for 2 h to give 70% 2-[6-[5-fluoro-2-[4-(piperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-pyridyl]propan-2-ol dihydrochloride II·2HCl (R = H). II·2HCl (R = H) and 2-[6-[2-[3-chloro-4-(piperazin-1-yl)anilino]-5-fluoropyrrolo[2,3-d]pyrimidin-7-yl]-2-pyridyl]propan-2-ol dihydrochloride (III) showed IC50 of 0.010μM, resp., against human Weel kinase. The experimental process involved the reaction of 1-Ethylpiperidin-4-amine dihydrochloride(cas: 357935-97-8).Computed Properties of 357935-97-8
The Article related to pyrrolopyrimidine preparation treatment cancer, wee1 kinase plk1 kinase inhibitor pyrrolopyrimidine preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Computed Properties of 357935-97-8
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem