Methanesulfonyl chloride → 3,6-Dihydro-4-methyl-2-[(methylsulfonyl)imino]-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

HRID 1789581Notes

Reaction equation

HRID 1789581 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.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:8][C:6]1[NH:7][C:2](=[N:1][S:29]([CH3:28])(=[O:31])=[O:30])[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]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 139572692-Amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester

Product 1

HCID 1363937023,6-Dihydro-4-methyl-2-[(methylsulfonyl)imino]-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (600 mg, 1.59 mmoles, see Example 2) in dichloromethane (5 ml) and pyridine (1.0 ml) was cooled to 0° C. under argon and was treated dropwise with methanesulfonyl chloride (0.42 ml, 5.26 mmoles). A catalytic amount of 4-dimethylamionpyridine was added and the reaction was allowed to warm to room temperature. After stirring overnight, the reaction was diluted with ethyl acetate and was washed with 1N hydrochloric acid, sodium bicarbonate and brine. It was dried over anhydrous magnesium sulfate and the solvent was evaporated to provide a colorless residue. Crystallization from ether-hexanes provided the title compound as a colorless crystalline material, melting point 139°-140.5° C.

Workup

  1. additionA catalytic amount of 4-dimethylamionpyridine was added
  2. temperatureto warm to room temperature
  3. washwas washed with 1N hydrochloric acid, sodium bicarbonate and brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customto provide a colorless residue
  7. customCrystallization from ether-hexanes

Sources & evidence

ORD record
ord-4d6ffa2e165a44e7922bf837ea8c5c06
Source dataset
uspto-grants-1987_08
Patent number
US04689414

Reaction notes

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