Benzene → 1,6-Dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1722401Notes

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(CC)CC)C.[C:32](Cl)(Cl)=[O:33].C1C=CC=CC=1.[CH2:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[Cl-].[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[N:8]([C:32]([NH:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:33])[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]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution 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 dry triethylamine (6.27 ml, 45 mmol) in dichloromethane (45 ml) in an ice bath under argon was treated with a 1.2M solution of phosgene in benzene (15.0 ml, 18.0 mmol) via syringe. After stirring 4.0 hours at 0° C., the reaction was treated with benzyl amine (2.46 ml, 22.5 mmol) and stirred at ambient temperature overnight. The reaction was treated with water and saturated sodium chloride. The organic phase was evaporated and flash chromatographed (3% ethyl acetate in dichloromethane) to give the title compound as a yellow foam (6.20 g) TLC (5% ethyl acetate/dichlorolmethane) major spot, Rf =0.70.

Workup

stirringstirred at ambient temperature overnight
customThe organic phase was evaporated
customflash chromatographed (3% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-9ff8d6bdff9f46049dac2c5f377ec371
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855301

Reaction notes

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