4-Piperidinol, 1-methyl- → HCID 9957766, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[CH3:30])[CH:5]=[CH:4][N:3]=1.[OH:31][CH:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1.CC(C)([O-])C.[K+]>>[CH3:30][C:10]1[CH:11]=[CH:12][C:13]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)=[O:17])=[CH:14][C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:31][CH:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[N:7]=1Participants
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 2-chloro-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.13 g), 4-hydroxy-N-methylpiperidine (0.087 g) and potassium tert-butoxide (1M in tert-butanol, 1.5 ml) was stirred and heated to 140° C. for 1 hour. The mixture was partitioned between water and methylene chloride and the organic phase was washed with brine, dried over sodium sulphate and evaporated. There was thus obtained the title compound as a solid (0.11 g); NMR Spectrum: (DMSOd6) 1.45 (m, 2H), 1.88 (m, 2H), 1.97 (m, 2H), 2.05 (s, 3H), 2.15 (s, 3H), 2.23 (m, 2H), 3.5 (m, 4H), 5.7 (m, 4H), 4.77 (m, 1H), 6.28 (d, 1H), 6.89 (m, 1H), 7.1 (m, 1H), 7.21 (m, 1H), 7.24 (s, 1H), 7.47 (m, 1H), 7.9 (m, 1H), 7.98 (d, 1H), 8.25 (m, 1H), 8.9 (s, 1H), 10.24 (s, 1H); Mass Spectrum: M+H+ 504.
Workup
- customThe mixture was partitioned between water and methylene chloride
- washthe organic phase was washed with brine
- dry with materialdried over sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-0274c958dc38470a8785716e6d430b93
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06846827B1
Reaction notes
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