4-Methoxy-6-methylpyrimidin-2-amine → HCID 13178326, compound

HRID 1074374Notes

Reaction equation

HRID 1074374 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])=[CH:12]1>C(#N)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:11][CH:12]=2)(=[O:21])=[O:22])=[O:25])[N:7]=1

Participants

4

Reactant 2

HCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 13178325Benzo[b]thiophene-3-sulfonyl isocyanate

Product 1

HCID 13178326HCID 13178326, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 25 ml of anhydrous acetonitrile containing 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine was added 2.4 g of benzothiophene-3-sulfonyl isocyanate with stirring. The mixture was heated to boiling, allowed to cool to room temperature and then stirred overnight. The resultant precipitate was filtered off and washed with ether to yield 2 g of the desired product, m.p. 180°-181° C. It showed absorption by NMR (60 MC) at 2.24 δ (6-CH3 group), 3.8 δ (4-OCH3), 6.2 δ (5-H on pyrimidine), 7-8 δ (aryl H's on benzo) and 8.3 δ (H on thiophene portion).

Workup

  1. temperatureThe mixture was heated
  2. stirringstirred overnight
  3. filtrationThe resultant precipitate was filtered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-ba48c14a848f4834bacf36f8099f44fb
Source dataset
uspto-grants-1983_07
Patent number
US04391627

Reaction notes

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