Thiophenol → (+/-)10-Amino-1 0-methyl-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one
Reaction equation
C1(S)C=CC=CC=1.[Sn](Cl)Cl.C(N(CC)CC)C.[N:18]([C:21]1([CH3:39])[CH2:27][CH2:26][CH2:25][CH2:24][N:23]2[C:28](=[O:38])[CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][N:33]=3)[N:31]=[C:22]12)=[N+]=[N-].[OH-].[Na+]>C(#N)C>[NH2:18][C:21]1([CH3:39])[CH2:27][CH2:26][CH2:25][CH2:24][N:23]2[C:28](=[O:38])[CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][N:33]=3)[N:31]=[C:22]12Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 23.9 mL (234.1 mmol) of thiophenol, 11.1 g (58.5 mmol) of tin (II) chloride and 24.5 mL (175.6 mmol) triethylamine in acetonitrile (300 mL) was stirred for 5 min at room temperature. 10-Azido-10-methyl-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one residue diluted in 90 mL of acetonitrile was added to this solution and the mixture was stirred for 1 h. A solution of sodium hydroxide (1M) was added and the mixture extracted with dichloromethane. After an acid-basic work-up, the residue was chromatographed on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 95/5 to afford 6.3 g (58%) of a yellow solid.
Workup
- additionwas added to this solution
- stirringthe mixture was stirred for 1 h
- extractionthe mixture extracted with dichloromethane
- customAfter an acid-basic work-up, the residue was chromatographed on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 95/5
Sources & evidence
- ORD record
- ord-88841715387948218de805d8daaddbe7
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198287B2
Reaction notes
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