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Benzyl isocyanate → N-(4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)-N'-benzylurea

HRID 251494
Notes
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Reaction equation

HRID 251494 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:26]3[C:25]([NH2:27])=[N:24][CH:23]=[N:22][C:21]=3[N:20]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:19]=2)=[CH:14][C:13]=1[O:33][CH3:34].C(N(CC)C(C)C)(C)C>ClCCl>[NH2:27][C:25]1[C:26]2[C:18]([C:15]3[CH:16]=[CH:17][C:12]([NH:11][C:9]([NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[C:13]([O:33][CH3:34])[CH:14]=3)=[CH:19][N:20]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[C:21]=2[N:22]=[CH:23][N:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 76639Benzyl isocyanateHCID 81531DiisopropylethylamineHCID 539252325-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 54264130N-(4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)-N'-benzylurea

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Procedure

Benzylisocyanate (24 uL, 0.194 mmol) in dichloromethane (1 mL) was added dropwise to a stirring solution of 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.155 mmol) in N,N-diisopropylethylamine (153 uL, 0.881 mmol) and methylene chloride (2 mL) under nitrogen. The resulting mixture was stirred for 24 hours. The solvent was evaporated and the solid was purified by preparative TLC using dichloromethane/methanol (95:5) as the mobile phase to give N-(4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)-N′-benzylurea. 1H NMR (CDCl3) δ 1.78 (m, 2H), 1.90 (m, 4H), 2.26 (m, 2H), 3.86 (s, 3H), 4.48 (d, J=6 Hz, 3H), 5.24 (m, 4H), 6.93 (s, 1H), 6.98 (s, 1H), 7.00 (s, 1H), 7.04 (d, J=8 Hz, 1H), 7.29 (m, 5H), 8.17 (d, J=8 Hz, 1H), 8.31 (s, 1H); LC/MS (MH+=457).

Workup

  1. customThe solvent was evaporated
  2. customthe solid was purified by preparative TLC

Sources & evidence

ORD record
ord-00c52d3cec7d474593a74c0a00ae95da
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863444B2

Reaction notes

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