Methylamine → 1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[C@@H:20]3[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[C@@H:22]([OH:30])[C@H:21]3[OH:31])=[C:13]([NH:32][CH2:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:12]=2)[CH:10]=1)=O)C.[CH3:47][NH2:48]>>[CH3:47][NH:48][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[C@@H:20]3[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[C@@H:22]([OH:30])[C@H:21]3[OH:31])=[C:13]([NH:32][CH2:33][CH:34]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:12]=2)[CH:10]=1)=[O:3]Participants
3
Reactant 2
Product 1
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 1-[9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.07 g, 0.112 mmol) and 40% aqueous methyl amine solution (3 ml) is heated to 65° C. for 12 h. The reaction mixture is concentrated in vacuo and purification of the crude residue by chromatography on silica eluting with 4% methanol in chloroform yields the title compound.
Workup
- concentrationThe reaction mixture is concentrated in vacuo and purification of the crude residue by chromatography on silica eluting with 4% methanol in chloroform
Sources & evidence
- ORD record
- ord-5c997ee62fee40d7b5f47005ca4caa67
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318750B2
Reaction notes
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