4-Nitrophenyl chloroformate → 6-(4-Cyanophenyl)-2-methoxy-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl) ester

HRID 570867Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]=[C:8]([O:12][CH3:13])[NH:9][C:10]=1[CH3:11])=[O:4].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl.N1C=CC=CC=1>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][C:23]([N:7]2[CH:6]([C:14]3[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=3)[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:10]([CH3:11])[N:9]=[C:8]2[O:12][CH3:13])=[O:24])=[CH:31][CH:30]=1)([O-:34])=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

Intermediate 4 (1.56 g, 5.46 mmol) was dissolved in a mixture of DCM (25 mL) and pyridine (10 mL) and cooled using an ice bath. A solution of 4-nitrophenyl chloroformate (705 mg, 3.50 mmol) in DCM (25 mL) was added over 30 minutes. The reaction mixture was stirred for 1 hour at 0° C. and then the solvent was removed in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-20% EtOAc in cyclohexane to gave the title compound as a yellow solid. The product thus obtained was used in the subsequent step without further analysis (2.0 g).

Workup

temperaturecooled
customthe solvent was removed in vacuo
customThe resulting residue was purified by silica gel chromatography
washeluting with a gradient of 0-20% EtOAc in cyclohexane

Sources & evidence

ORD record: ord-341452b4ab6b4c179eb5f77f5ebecceb
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023855B2

Reaction notes

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