Water → Phenylmethyl N-[4-[(6-chloro-4-pyrimidinyl)oxy]-2,5-difluorophenyl]carbamate

HRID 2066284Notes

Reaction equation

HRID 2066284 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([OH:18])=[CH:13][C:12]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([O:18][C:26]2[N:25]=[CH:24][N:23]=[C:22]([Cl:21])[CH:27]=2)=[CH:13][C:12]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 57470872HCID 57470872, compound

Product 1

HCID 57470873Phenylmethyl N-[4-[(6-chloro-4-pyrimidinyl)oxy]-2,5-difluorophenyl]carbamateYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl(2,5-difluoro-4-hydroxyphenyl)carbamate (4.90 g) was dissolved in N,N-dimethylformamide (30 ml), then 4,6-dichloropyrimidine (2.61 g) and potassium carbonate (3.63 g) were added thereto at room temperature, followed by stirring for 2 hr. Water (90 ml) was added to the reaction mixture to precipitate crystals. The crystals were collected by filtration and washed with water (30 ml, 6 times). The crystals were hot air-dried at 60° C. for 2 days to provide the titled compound as pale brown crystals (6.108 g, 89%).

Workup

  1. customat room temperature
  2. customto precipitate crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water (30 ml, 6 times)
  5. customThe crystals were hot air-dried at 60° C. for 2 days

Sources & evidence

ORD record
ord-a9b9d6933da74ae49ebfa1ff69be896e
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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