Sodium hydride → 4-Chloro-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-2-amine

HRID 1958616Notes

Reaction equation

HRID 1958616 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1)[OH:4].[H-].[Na+].[NH2:22][C:23]1[N:28]=[C:27](Cl)[CH:26]=[C:25]([Cl:30])[N:24]=1>C1COCC1>[Cl:30][C:25]1[CH:26]=[C:27]([O:4][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)[C:2]([F:18])([F:19])[F:1])[N:28]=[C:23]([NH2:22])[N:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 666492512,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol

Product 1

HCID 866143104-Chloro-6-(2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy)pyrimidin-2-amineYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2,2,2-Trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol (0.15 g, 0.563 mmol) was treated with NaH (60% in mineral oil, 45 mg, 1.12 mmol) in dry THF (5 ml) for 30 minutes. 2-Amino-4,6-dichloropyrimidine (92 mg, 0.5633 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 0.16 g of 4-chloro-6-(2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethoxy)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-4ce602cf6e2e46a0812ec2c82ac05864
Source dataset
uspto-grants-2013_04
Patent number
US08410121B2

Reaction notes

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