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

HRID 2265715Notes

Reaction equation

HRID 2265715 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([F:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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>[Cl:21][C:22]1[CH:27]=[C:26]([O:8][C:6]2[C:5]([F:9])=[CH:4][C:3]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:2]([F:1])[CH:7]=2)[N:25]=[CH:24][N:23]=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-ca63e4ef09a54a64a99e661bb72df5c1
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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