2-Amino-4,6-dimethoxypyrimidine → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(dimethylaminosulfonyloxy)benzenesulfonamide

HRID 482797Notes

Reaction equation

HRID 482797 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH3:12][N:13]([CH3:30])[S:14]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([N:27]=[C:28]=[O:29])(=[O:26])=[O:25])(=[O:16])=[O:15]>C(Cl)Cl>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:28]([NH:27][S:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][S:14]([N:13]([CH3:30])[CH3:12])(=[O:15])=[O:16])(=[O:25])=[O:26])=[O:29])[N:7]=1

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 134731272-(Dimethylaminosulfonyloxy)benzenesulfonyl isocyanate

Product 1

HCID 13473128N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(dimethylaminosulfonyloxy)benzenesulfonamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.46 g (0.003 mole) 2-amino-4,6-dimethoxypyrimidine in 5 ml methylene chloride was added 1.2 g (0.004 mole) 2-(dimethylaminosulfonyloxy)-benzenesulfonyl isocyanate. The reaction exothermed (18°-26° C.) and was then stirred at room temperature 3 hours. The solvent was evaporated under reduced pressure. The resultant mixture was triturated with diethyl ether and filtered to give 1.2 g of a white solid, m.p. 165°-168° C. The infrared spectrum shows absorption bands at 1710, 1380, 1170 cm-1.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe resultant mixture was triturated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-1a74b1b6e955422ea447d64bb301bce6
Source dataset
uspto-grants-1986_03
Patent number
US04576633

Reaction notes

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