4-Methoxy-6-methylpyrimidin-2-amine → HCID 15591263, compound

HRID 1462841Notes

Reaction equation

HRID 1462841 reaction equation
[C:1]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11])([O:3][CH3:4])=[O:2].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH2:25])[N:19]=1>C(#N)C.CCOCC>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][C:14]([NH:13][S:10]([C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[C:1]([O:3][CH3:4])=[O:2])(=[O:11])=[O:12])=[O:15])[N:19]=1

Participants

5

Reactant 2

HCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 15591262Methyl 2-[(oxomethylidene)sulfamoyl]cyclopent-1-ene-1-carboxylate

Product 1

HCID 15591263HCID 15591263, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

The sulfonyl isocyanate product (5 g) of Example 3 was diluted to a concentration of 1.5M with dry acetonitrile and 2.0 ml of this solution was added to a stirred suspension of 0.31 g 4-methoxy-6-methylpyrimidine-2-amine in 4.0 ml of dry acetonitrile under a nitrogen atmosphere at room temperature. After stirring several hours, the mixture was diluted with ether to precipitate the product which was collected by filtration and dried; m.p. 161°-163°. An infrared spectrum (nujol) exhibited absorptions at 1730 and 1700 cm-1, and an NMR (90 MHz) in CDCl3 solution exhibited absorptions at 2.1 (CH2), 2.45 (CH3), 3.0 (CH2 ×2), 3.75 (CH3O), 3.95 (CH3O), 6.3 (CH), 7.9 (NH), 13.8 (NH), ppm indicating the title compound.

Workup

  1. customto precipitate the product which
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-4d4c9ef9081746358df5896ae0534c42
Source dataset
uspto-grants-1984_07
Patent number
US04461640

Reaction notes

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