Ammonia → 2-{4-[4-({4-[2-methyl-1-(1-methylethyl)-1H-imidazol-5-yl]pyrimidin-2-yl}amino)phenyl]piperazin-1-yl}-2-oxoethanol

HRID 1441309Notes

Reaction equation

HRID 1441309 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:35]=[CH:34][C:17]([NH:18][C:19]3[N:24]=[C:23]([C:25]4[N:29]([CH:30]([CH3:32])[CH3:31])[C:28]([CH3:33])=[N:27][CH:26]=4)[CH:22]=[CH:21][N:20]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(=O)C.N>CO>[OH:4][CH2:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:35]=[CH:34][C:17]([NH:18][C:19]3[N:24]=[C:23]([C:25]4[N:29]([CH:30]([CH3:32])[CH3:31])[C:28]([CH3:33])=[N:27][CH:26]=4)[CH:22]=[CH:21][N:20]=3)=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 686898132-{4-[4-(2-Acetoxyacetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Product 1

HCID 112705002-{4-[4-({4-[2-methyl-1-(1-methylethyl)-1H-imidazol-5-yl]pyrimidin-2-yl}amino)phenyl]piperazin-1-yl}-2-oxoethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-{4-[4-(2-Acetoxyacetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine (Example 21; 330 mg) was stirred in MeOH (5 ml) at room temperature and 7N ammonia in MeOH (1.6 ml) was added. After 28 hours, the reaction was evaporated under reduced pressure. Chromatography on silica gel using MeOH:DCM (4:96 to 5:95), yielded the title compound as a yellow solid. (108 mg 36%). NMR: 1.39 (d, 6H), 2.46 (s, 3H), 3.05 (b s, 4H), 3.48 (b s, 2H), 3.61 (b s, 2H), 4.12 (d, 2H), 4.57 (t, 1H), 5.69 (septuplet, 1H), 6.92 (d, 2H), 6.95 (d, 1H), 7.38 (s, 1H), 7.47 (d, 2H), 8.31 (d, 1H), 9.15 (s, 1H); m/z 436.

Workup

  1. customthe reaction was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a3c34f467ef486aac1c149bd7c1d186
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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