Benzene → 1-Carbamoyl-1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester
Reaction equation
[CH3:1][O:2][C:3]1[NH:4][C:5]([CH3:24])=[C:6]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.C([N:27]([CH2:30]C)CC)C.C(Cl)(Cl)=[O:33].C1C=CC=CC=1.[OH-].[NH4+]>ClCCl>[C:30]([N:8]1[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:6]([C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])=[C:5]([CH3:24])[N:4]=[C:3]1[O:2][CH3:1])(=[O:33])[NH2:27]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A soluton of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (5.00 g, 15.0 mmol; see Example 2A) and triethylamine (5.88 g; 45.0 mmol) in dichloromethane (45 ml) at 0° C. under argon was treated via syringe with a 1.2M solution of phosgene in benzene (15.0 ml, 18.0 mmol). After stirring at 0° C. for 3.5 hours, the reaction was treated with concentrated ammonium hydroxide (1.52 ml, 22.5 mmol). After two hours at room temperature, the reaction was treated with more concentrated ammonium hydroxide (0.5 ml, 7.5 mmol) and stirred at room temperature overnight. The reaction was then diluted with dichloromethane and washed with water and saturated sodium chloride. The organic phase was concentrated and flash chromatographed to give the title compound as a brittle yellow foam (2.83 g).
Workup
- waitAfter two hours at room temperature
- stirringstirred at room temperature overnight
- washwashed with water and saturated sodium chloride
- concentrationThe organic phase was concentrated
- customflash chromatographed
Sources & evidence
- ORD record
- ord-1bd9695e2713479d84d0f940e9463a98
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855301
Reaction notes
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