4-Methoxy-6-methylpyrimidin-2-amine → N-2-biphenylylsulfonyl-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea

HRID 615532Notes

Reaction equation

HRID 615532 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[C:11]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([N:20]=[C:21]=[O:22])(=[O:19])=[O:18]>ClCCl.C1(C)C=CC=CC=1>[C:11]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH:20][C:21]([NH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1)=[O:22])(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 131033202-Biphenylylsulfonylisocyanate

Product 1

HCID 13103321N-2-biphenylylsulfonyl-N'-(4-methoxy-6-methylpyrimidin-2-yl)ureaYield 86.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

13.9 g of 2-amino-4-methoxy-6-methylpyrimidine were dissolved in 150 ml of dry dichloromethane. To this solution was added dropwise a solution of 28.5 g of 2-biphenylylsulfonyl isocyanate in 40 ml of toluene over an hour. During this addition, the internal temperature was maintained at room temperature. When the addition was finished, the mixture was stirred at room temperature for 10 hours to complete the reaction. After completion of the reaction, the mixture was concentrated to about half the volume by evaporating dichloromethane under reduced pressure. The resultant colorless crystals were filtered. The crystals were then washed with a small amount of ether and dried to obtain 34.6 g of N-2-biphenylylsulfonyl-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea; m.p. 199°-202° C.

Workup

  1. additionDuring this addition
  2. additionWhen the addition
  3. customthe reaction
  4. customAfter completion of the reaction
  5. concentrationthe mixture was concentrated to about half the volume
  6. customby evaporating dichloromethane under reduced pressure
  7. filtrationThe resultant colorless crystals were filtered
  8. washThe crystals were then washed with a small amount of ether
  9. customdried

Sources & evidence

ORD record
ord-4f7c27d4a48f42478a28fb37a399eb0d
Source dataset
uspto-grants-1985_02
Patent number
US04500342

Reaction notes

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