Thionyl Chloride → 4-Chloro-5-(4-(chloromethyl)-2-fluorobenzyl)-6-methylpyrimidin-2-amine

HRID 2387834Notes

Reaction equation

HRID 2387834 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[N:11]=[C:10]([Cl:12])[C:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][C:15]=2[F:22])=[C:8]([CH3:23])[N:7]=1>C(Cl)Cl>[Cl:12][C:10]1[C:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][Cl:3])=[CH:16][C:15]=2[F:22])=[C:8]([CH3:23])[N:7]=[C:6]([NH2:5])[N:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86633403(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)methanol

Product 1

HCID 866334044-Chloro-5-(4-(chloromethyl)-2-fluorobenzyl)-6-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.078 mL) was added to a stirred solution of the product from step (i) (0.30 g) in DCM (5 mL). The mixture was stirred at rt for 1 h and then the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography to give the subtitle compound, 0.13 g.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-3d27aa23cbb0464cb04fc0d3b5244595
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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