Acetic Anhydride → 2-(Acetylamino)-3,6-dihydro-4-methyl-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

HRID 1789580Notes

Reaction equation

HRID 1789580 reaction equation
[NH2:1][C:2]1[N:3]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[C:28]([NH:1][CH:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:3]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:30])[CH3:29]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 139572692-Amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester

Product 1

HCID 139572712-(Acetylamino)-3,6-dihydro-4-methyl-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (550 mg, 1.46 mmoles, see Example 2) in dichloromethane (5.0 ml) and pyridine (0.5 ml) was treated with acetic anhydride (0.3 ml) and the reaction was allowed to stir at room temperature for 1 hour. The colorless reaction mixture was diluted with ethyl acetate and was washed with 5% citric acid, sodium bicarbonate solution and brine. It was dried over anhydrous magnesium sulfate and evaporated to provide a colorless foam. Crystallization from ether-hexanes provided the title compound as a colorless solid, melting point 154.5°-156° C.

Workup

  1. washwas washed with 5% citric acid, sodium bicarbonate solution and brine
  2. dry with materialIt was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customto provide a colorless foam
  5. customCrystallization from ether-hexanes

Sources & evidence

ORD record
ord-99317e12e9e34e248ca2fd650b9d5d3c
Source dataset
uspto-grants-1987_08
Patent number
US04689414

Reaction notes

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