Sodium hydride → 4-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amine

HRID 1958610Notes

Reaction equation

HRID 1958610 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].[NH2:17][C:18]1[N:23]=[C:22](Cl)[CH:21]=[C:20]([Cl:25])[N:19]=1>C1COCC1>[Cl:25][C:20]1[CH:21]=[C:22]([O:14][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[C:10]([F:11])([F:12])[F:13])[N:23]=[C:18]([NH2:17])[N:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 610879271-(3,4-Difluorophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 866143094-Chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)pyrimidin-2-amineYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1-(3,4-Difluorophenyl)-2,2,2-trifluoroethanol (0.1 g, 0.471 mmol) was treated with NaH (60% in mineral oil, 38 mg, 0.943 mmol) in dry THF (3 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (77 mg, 0.471 mmol) was added and the mixture was stirred at 50° C. for 6 hours. The mixture was quenched with water and extracted with methylenechloride (2×). The organics were combined, washed with water, then brine, dried over MgSO4, and concentrated to give 0.14 g of 4-chloro-6-(1-(3,4-difluorophenyl)-2,2,2-trifluoroethoxy)-pyrimidin-2-amine.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with methylenechloride (2×)
  3. washwashed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca0531d29b85406d8d4f30fe3fd3be38
Source dataset
uspto-grants-2013_04
Patent number
US08410121B2

Reaction notes

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