Thionyl Chloride → 6-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-4-amine

HRID 77471Notes

Reaction equation

HRID 77471 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]([CH2:20]O)[CH:15]=2)[CH:9]=[CH:10][C:11]=1[Cl:12]>C(Cl)(Cl)Cl>[Cl:3][CH2:20][C:16]1[N:17]=[CH:18][N:19]=[C:14]([NH:13][C:8]2[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([Cl:5])[CH:7]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86679759(6-(3,4-Dichlorophenylamino)pyrimidin-4-yl)methanol

Product 1

HCID 866797606-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (0.184 mL, 2.52 mmol) was added dropwise to a stirred solution of (6-((3,4-dichlorophenyl)amino)pyrimidin-4-yl)methanol (0.17 g, 0.629 mmol) in chloroform at 0° C. The mixture was allowed to warm to room temperature and further stirred for 18 h. After concentration, the crude product 6-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-4-amine (0.08 g, 75%) was used in the next step without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.85 (1H, br. s.), 8.81 (1H, s), 8.20 (1H, s), 7.64 (2H, s), 7.11 (1H, s), 4.76 (2H, s). LCMS: R.T.=3.48; [M+H]+=287.91.

Workup

  1. concentrationAfter concentration
  2. customthe crude product 6-(chloromethyl)-N-(3,4-dichlorophenyl)pyrimidin-4-amine (0.08 g, 75%) was used in the next step without purification
  3. customR.T.=3.48

Sources & evidence

ORD record
ord-f7365d4719084d909f08fe4a335a5cf1
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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