2-Amino-4,6-dimethoxypyrimidine → HCID 13489818, compound

HRID 1193445Notes

Reaction equation

HRID 1193445 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.[O:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])=[CH:15][CH:14]=[N:13]1>C(#N)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:27]([NH:26][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]2[O:12][N:13]=[CH:14][CH:15]=2)(=[O:25])=[O:24])=[O:28])[N:7]=1

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 13489817HCID 13489817, compound

Product 1

HCID 13489818HCID 13489818, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 2.5 g of 2-amino-4,6-dimethoxypyrimidine in 25 ml of acetonitrile was added 4 g of crude 2-(isoxazol-5-yl)benzenesulfonyl isocyanate prepared in Example 7. The resulting suspension was warmed at 40° C. for about 3 minutes to form a solution. The solution was stirred at room temperature for 10 hours, then concentrated in vacuo to give a viscous oil. The oil was chromatographed in a dry column of silica gel with ethyl acetate as eluant. The first fraction from the column was concentrated in vacuo to yield a solid. The solid was washed 1×10 ml of acetonitrile and suction dried to yield 0.5 g of the title compound; m.p. 183°-187° C. The IR spectrum showed a carbonyl absorption at 1710 cm-1 indicative of a sulfonylurea.

Workup

  1. customto form a solution
  2. concentrationconcentrated in vacuo
  3. customto give a viscous oil
  4. customThe oil was chromatographed in a dry column of silica gel with ethyl acetate as eluant
  5. concentrationThe first fraction from the column was concentrated in vacuo
  6. customto yield a solid
  7. washThe solid was washed 1×10 ml of acetonitrile and suction
  8. customdried

Sources & evidence

ORD record
ord-d0daeb73ed934039b5b58d195242fb3e
Source dataset
uspto-grants-1989_03
Patent number
US04810282

Reaction notes

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