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

HRID 1617180Notes

Reaction equation

HRID 1617180 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 Ih 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-de260b359fb44187a427c5a7e6fd77f5
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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