Ethyl 5-amino-2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate → 2-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide
Reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:25]=[C:24]3[C:20]([NH:21][C:22](=[O:34])[N:23]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[C:19]([C:35]([O:37]CC)=O)[N:18]=2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[NH2:40]C1C(C(OCC)=O)=NC(NC2C=CC=C(CO[Si](C(C)(C)C)(C)C)C=2)=NC=1NC1C=CC=CC=1OC>ClCCl>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:25]=[C:24]3[C:20]([NH:21][C:22](=[O:34])[N:23]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[C:19]([C:35]([NH2:40])=[O:37])[N:18]=2)[CH:13]=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (0.242 g, 0.462 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.525 g, 3.23 mmol) in dichloromethane (15 mL) were reacted according to General Procedure F and purified using biotage chromatography (10 to 90% EtOAc in hexanes) to afford the title compound (0.180 g, 71%). MS (ESI) m/z 550.5 [M+1]+.
Workup
- custompurified
Sources & evidence
- ORD record
- ord-e3bf09f143a0494abfe5168b2452e120
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383634B2
Reaction notes
Loading…