Thionyl Chloride → 2-(4-(4-(chloromethyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)piperidin-1-yl)-5-ethylpyrimidine

HRID 80675Notes

Reaction equation

HRID 80675 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([CH2:24]O)[CH:17]=[N:16]3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].S(Cl)([Cl:28])=O>ClCCl>[Cl:28][CH2:24][C:18]1[CH:17]=[N:16][N:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:6]3[N:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=3)[CH2:10][CH2:11]2)[C:19]=1[C:20]([F:23])([F:22])[F:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57708404(1-(1-(5-Ethylpyrimidin-2-yl)piperidin-4-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 577083712-(4-(4-(chloromethyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)piperidin-1-yl)-5-ethylpyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)methanol (0.13 g, 0.366 mmol) in dichloromethane (3 mL) was added thionyl chloride (1.2 mL) and the solution was stirred at room temperature for 2 h. The reaction was concentrated in vacuo and the crude product was used in the next step without further purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-cd98ff68a93b412595b8d02a1c806812
Source dataset
uspto-grants-2014_09
Patent number
US08846675B2

Reaction notes

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