2-Amino-4,6-dimethoxypyrimidine → HCID 19899630, compound

HRID 1029325Notes

Reaction equation

HRID 1029325 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[O:7][S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9].[NH2:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=1>ClCCl>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[O:7][S:8]([NH:11][C:12]([NH:18][C:19]1[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[N:24]=1)=[O:13])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 19899631HCID 19899631, compound

Product 1

HCID 19899630HCID 19899630, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 5.6 g (0.02 mol) of the product of Example 1 in 20 ml of dichloromethane is added dropwise at 0° C. to 3.1 g (0.02 mol) of 2-amino-4,6-dimethoxypyrimidine in 30 ml of dichloromethane. The reaction mixture is allowed to reach room temperature, and stirring is continued for 24 hours. The reaction solution is diluted using 100 ml of dichloromethane and washed with 50 ml of 1N hydrochloric acid and 50 ml of water. The organic phase is dried using sodium sulfate, and the solvent is removed on a rotary evaporator. The viscous oil which remains is crystallized by trituration with diethyl ether. 7.7 g (89% of theory) of 1-[2-(2-chloroethoxy)phenoxy-sulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea of melting point 132°-134° C. are obtained.

Workup

  1. customto reach room temperature
  2. additionThe reaction solution is diluted
  3. washwashed with 50 ml of 1N hydrochloric acid and 50 ml of water
  4. customThe organic phase is dried
  5. customthe solvent is removed on a rotary evaporator
  6. customThe viscous oil which remains is crystallized by trituration with diethyl ether

Sources & evidence

ORD record
ord-50116df81bf34d6bb76d9393142b0a1f
Source dataset
uspto-grants-1992_04
Patent number
US05102443

Reaction notes

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