4-Methoxy-6-methylpyrimidin-2-amine → N-[(4-Methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]-4-nitrothiophene-2-sulfonamide

HRID 1248387Notes

Reaction equation

HRID 1248387 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[N+:11]([C:14]1[CH:15]=[C:16]([S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20])[S:17][CH:18]=1)([O-:13])=[O:12]>C(#N)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:23]([NH:22][S:19]([C:16]2[S:17][CH:18]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)(=[O:21])=[O:20])=[O:24])[N:7]=1

Participants

4

Reactant 2

HCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 202157024-Nitrothiophene-2-sulfonyl isocyanate

Product 1

HCID 13203353N-[(4-Methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]-4-nitrothiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 25 ml of anhydrous acetonitrile was added 2.4 g of 4-nitrothiophene-2-sulfonyl isocyanate with stirring at ambient temperature. After stirring for sixteen hours, the mixture was filtered and the precipitate washed with 1-chlorobutane. It melted at 155° with decomposition and showed an infrared absorption spectrum with peaks at 1700, 1620 and 1570 cm-1 consistent for the desired structure.

Workup

  1. stirringAfter stirring for sixteen hours
  2. filtrationthe mixture was filtered
  3. washthe precipitate washed with 1-chlorobutane
  4. customan infrared absorption spectrum with peaks at 1700, 1620 and 1570 cm-1 consistent for the desired structure

Sources & evidence

ORD record
ord-db633a9a3c964f4da7ac06c2cddf449e
Source dataset
uspto-grants-1985_06
Patent number
US04523943

Reaction notes

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