Imidazole → 7-{4-[2-(1H-1-imidazolyl)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 51602Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CS(O[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:23]3[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=3[C:21]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:31][CH:30]=3)=[CH:20]2)[CH2:15][CH2:14]1)(=O)=O.[H-].[Na+]>CN(C)C=O>[N:1]1([CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=4[C:21]([C:29]4[CH:30]=[CH:31][C:32]([O:35][C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)=[CH:33][CH:34]=4)=[CH:20]3)[CH2:15][CH2:14]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

Imidazole (0.070 g, 1.03 mmol) was added into a solution of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}ethyl methanesulfonate (0.052 g, 0.10 mmol) in N,N-dimethylformamide (2 mL). The mixture was stirred at 40° C. for 5 hours. 60% Sodium hydride in mineral oil (0.021 g, 052 mmol) was added and the mixture was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by preparative RP-HPLC to yield 7-{4-[2-(1H-1-imidazolyl)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.030 g, 0.063 mmol) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.30(s, 1H), 7.55(br, 1H), 7.44(d, 2H), 7.42(t, 2H), 7.16(t, 1H), 7.08(m, 6H), 6.95(br, 1H), 5.49(br, 2H), 4.72(m, 1H), 4.01(t, 2H), 1.99-1.71 (m, 11H); RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% over 10 min acetonitrile-0.05M ammonium acetate, 1 mL/min) Rt 9.18 min; MS: MH+ 479.

Workup

stirringthe mixture was stirred at ambient temperature overnight
customThe solvent was removed under reduced pressure
customthe residue was purified by preparative RP-HPLC

Sources & evidence

ORD record: ord-3407a783e8e6424691d607de940a6385
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Reaction notes

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