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

HRID 51602
Notes
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Reaction equation

HRID 51602 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 227363462-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}ethyl methanesulfonate

Product 1

HCID 227363807-{4-[2-(1H-1-imidazolyl)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 63%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes