Thionyl Chloride → 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine

HRID 77448

Reaction equation

HRID 77448 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][N:14]=2)=[CH:8][CH:7]=1>C(Cl)Cl>[Cl:3][CH2:19][C:16]1[CH:15]=[N:14][C:13]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86679732(2-(4-Chlorophenylamino)pyrimidin-5-yl)methanol

Product 1

HCID 866797335-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amineYield 112.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (0.427 mL, 5.86 mmol) was added to a suspension of (2-((4-chlorophenyl)amino)pyrimidin-5-yl)methanol (0.23 g, 0.976 mmol) in DCM (10 mL) cooled to 0° C. The mixture was stirred for 18 h while warming to room temperature. The reaction mixture was concentrated and the residue triturated with ether to give 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine as a pale yellow solid (0.28 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.03 (s, 1H), 8.60 (s, 2H), 7.85-7.64 (m, 2H), 7.41-7.20 (m, 2H), 4.77 (s, 2H).

Workup

  1. temperaturewhile warming to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue triturated with ether

Sources & evidence

ORD record
ord-9b0ce0adbb5b42b7a928ee1ccca61412
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Linked notes

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