4-Nitrophenyl chloroformate → (+/-)-4-Oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepine-10-carboxylic acid (4-nitro-phenyl) ester
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]3[C:16](=[O:18])[CH:17]=2)=[N:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31]>O1CCCC1>[N+:39]([C:36]1[CH:35]=[CH:34][C:33]([O:32][C:30]([CH:15]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]3[C:16](=[O:18])[CH:17]=[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][N:3]=4)[N:8]=[C:9]23)=[O:31])=[CH:38][CH:37]=1)([O-:41])=[O:40]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
To a solution of 0.500 g (2.06 mmol) of 2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one (step 6.1 of example 6) in dry tetrahydrofuran (20 mL) under argon at −40° C. was added 2.27 mL (2.27 mmol) of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran). The solution was stirred at −50° C. for 10 min and 1.04 g (5.16 mmol) of 4-nitrophenyl chloroformate diluted in 3 ml of dry tetrahydrofuran was added. The mixture was quenched with the addition of a saturated solution of ammonium chloride and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The residue was used as such for the next step.
Workup
- additionwas added
- customThe mixture was quenched with the addition of a saturated solution of ammonium chloride
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3632d5c3523443c89e6b80a90038f12b
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614219B2
Reaction notes
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