Thionyl Chloride → HCID 117818892, compound

HRID 1753226Notes

Reaction equation

HRID 1753226 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([CH2:10]O)[C:5]=1[CH3:12].S(Cl)([Cl:16])=O>C(Cl)Cl>[Cl:16][CH2:10][C:6]1[C:5]([CH3:12])=[C:4]([O:3][CH:2]([F:13])[F:1])[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 117819035HCID 117819035, compound

Product 1

HCID 117818892HCID 117818892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-(difluoromethoxy)-5-methylpyrimidin-4-yl)methanol 49 (15 g, 78.94 mmol) dissolved in DCM (150 ml) added thionyl chloride (8.59 ml, 118.42 mmol). The reaction mixture was stirred for 4 h at RT. The solvent was removed under vacuum pump to afford 4-(chloromethyl)-6-(difluoromethoxy)-5-methylpyrimidine 50 as a brown solid. Yield: 14 g (85%); 1H NMR (400 MHz, DMSO-d6) δ=8.74 (s, 1H), 7.77 (t, 1H, J=95.4 Hz), 4.81 (s, 2H), 2.24 (s, 3H).

Workup

  1. customThe solvent was removed under vacuum pump

Sources & evidence

ORD record
ord-5d3ba8567af54921a4f233015853fa43
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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