Sodium hydride → 4-Chloro-6-[2,2,2-trifluoro-1-[2-(3-trifluoromethyl-pyrazol-1-yl)phenyl]-ethoxy]-pyrimidine-2-ylamine

HRID 2233458Notes

Reaction equation

HRID 2233458 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[F:10][C:11]([F:30])([F:29])[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[N:21]1)[OH:13].[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[CH:5]=[C:4]([O:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[N:21]2)[C:11]([F:30])([F:29])[F:10])[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 866210922,2,2-Trifluoro-1-[2-(3-trifluoro methyl-pyrazol-1-yl)-phenyl]-ethanol

Product 1

HCID 866210934-Chloro-6-[2,2,2-trifluoro-1-[2-(3-trifluoromethyl-pyrazol-1-yl)phenyl]-ethoxy]-pyrimidine-2-ylamineYield 106.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
42.5 °C

Procedure

2-Amino-4,6-dichloro pyrimidine (0.074 g, 0.45 mmol), 2,2,2-trifluoro-1-[2-(3-trifluoro methyl-pyrazol-1-yl)-phenyl]-ethanol (0.140 g, 0.45 mmol), and NaH (0.022 g, 0.59 mmol) were added to anhydrous THF (10 ml) under nitrogen atmosphere. The reaction was stirred at 40-45° C. for 6 h, and then cooled to room temperature, and quenched with water (0.2 ml). The reaction mixture was concentrated to give crude 4-chloro-6-[2,2,2-trifluoro-1-[2-(3-trifluoromethyl-pyrazol-1-yl)phenyl]-ethoxy]-pyrimidine-2-ylamine (0.21 g, >90% pure by LCMS), which was directly used in the next step.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water (0.2 ml)
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-b9ffd8f319fe4846b4292134cec4d480
Source dataset
uspto-grants-2010_05
Patent number
US07709493B2

Reaction notes

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