Thionyl Chloride → 4-(Chloromethyl)-N-(4-fluorophenyl)-6-methylpyrimidine-2-amine

HRID 242149Notes

Reaction equation

HRID 242149 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([CH2:15]O)[CH:12]=[C:11]([CH3:17])[N:10]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>ClCCl>[Cl:20][CH2:15][C:13]1[CH:12]=[C:11]([CH3:17])[N:10]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59278633{2-[(4-Fluorophenyl)amino]-6-methylpyrimidin-4-yl}methanol

Product 1

HCID 592786484-(Chloromethyl)-N-(4-fluorophenyl)-6-methylpyrimidine-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 225 mg (0.96 mmol) of the compound from example 6A and 137 mg (1.16 mmol) of thionyl chloride are initially charged in 10 ml of dichloromethane and, after warming to RT, stirred at this temperature for 24 h. The solvent is removed on a rotary evaporator and the product that remains is directly reacted further.

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. customthe product that remains is directly reacted further

Sources & evidence

ORD record
ord-4600fafe061d4f6399db50d26ec7e638
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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