2-Amino-4,6-dimethoxypyrimidine → HCID 19899628, compound

HRID 1029326Notes

Reaction equation

HRID 1029326 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.[CH2:12]([O:15][C:16]1[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=1[O:18][S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20])[C:13]#[CH:14]>ClCCl>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:23](=[O:24])[NH:22][S:19]([O:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[O:15][CH2:12][C:13]#[CH:14])(=[O:21])=[O:20])[N:7]=1

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 86745610HCID 86745610, compound

Product 1

HCID 19899628HCID 19899628, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3.1 g (0.02 mol) of 2-amino-4,6-dimethoxypyrimidine are dissolved in 30 ml of dichloromethane, and 5.1 g (0.02 mol) of 2-propargyloxyphenoxysulfonyl isocyanate--dissolved in 20 ml of dichloromethane--are added at 0° C. After the reaction mixture has been stirred for 24 hours at room temperature, it is diluted with 50 ml of dichloromethane, washed with 50 ml of 1N hydrochloric acid and 50 ml of water, dried and evaporated. The oily residue crystallizes on trituration with diethyl ether. 7.4 g (91% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea of melting point 125°-126° C. are obtained.

Workup

  1. additionare added at 0° C
  2. washwashed with 50 ml of 1N hydrochloric acid and 50 ml of water
  3. customdried
  4. customevaporated
  5. customThe oily residue crystallizes on trituration with diethyl ether

Sources & evidence

ORD record
ord-1db84ea8b9624885aab63671a8b2501d
Source dataset
uspto-grants-1992_04
Patent number
US05102443

Reaction notes

Loading…