Thionyl Chloride → 6-(Chloromethyl)-N,N,5-trimethylpyrimidin-4-amine

HRID 1753223Notes

Reaction equation

HRID 1753223 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9]O)[C:4]=1[CH3:11].S(Cl)([Cl:15])=O>C(Cl)Cl>[Cl:15][CH2:9][C:5]1[N:6]=[CH:7][N:8]=[C:3]([N:2]([CH3:12])[CH3:1])[C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14306168(6-(Dimethylamino)-5-methylpyrimidin-4-yl)methanol

Product 1

HCID 143061696-(Chloromethyl)-N,N,5-trimethylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-(dimethylamino)-5-methylpyrimidin-4-yl)methanol (46) (40 g, 239 mmol) in DCM was added thionyl chloride (35 ml, 478 mmol). The reaction mixture was stirred for 4 h at RT. The solvent was removed under reduced pressure to afford 6-(Chloromethyl)-N,N,5-trimethylpyrimidin-4-amine (47) as a brown solid; Yield: 40 g (90.9%); NMR (400 MHz, DMSO-d6) δ=8.69 (s, 1H), 4.86 (s, 2H), 3.27 (s, 6H), 2.35 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0b9e4087df974ea3adb82da362c3a7fd
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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