2-Amino-4,6-dimethoxypyrimidine → HCID 13937618, compound

HRID 648860Notes

Reaction equation

HRID 648860 reaction equation
[CH3:1][N:2]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[C:8]=1[CH2:17][S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19])(=[O:6])=[O:5])[CH3:3].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([NH2:34])[N:27]=1>C(Cl)Cl>[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([NH:34][C:22]([NH:21][S:18]([CH2:17][C:8]2[C:7]([S:4]([N:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])=[CH:12][CH:11]=[CH:10][C:9]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:20])=[O:19])=[O:23])[N:27]=1

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 20143943HCID 20143943, compound

Product 1

HCID 13937618HCID 13937618, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the sulfonyl isocyanate from Example 16 (approximately 1.3 g) and 0.56 g of 4,6-dimethoxy-2-aminopyrimidine in 6 ml methylene chloride was stirred overnight at room temperature. The reaction mixture was then filtered and the filtrate concentrated in vacuo. Trituration of the residue with warm n-butyl chloride/ethyl acetate gave a cream-colored solid. The yield of the title compound, m.p. 175°-180°, was 1.1 g; IR(nujol): 1720, 1730 cm-1 ; NMR(CDCl3 /DMSO-d6): δ 2.8 (6H, s, SO2N(CH3)2), 3.7-4.0 (9H, s, CO2CH3 and OCH3 's), 5.8-6.0 (3H, two singlets, --CH2 -- and heterocyclic ring H), 7.55-8.4 (3H, m), 10.5 (1H, br s, NH), 12.5 (1H, br s, NH).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customTrituration of the residue with warm n-butyl chloride/ethyl acetate gave a cream-colored solid

Sources & evidence

ORD record
ord-ddd43df09212427c830dbcbcdb9a6fb6
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

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