Dimethylformamide → 4-Chloro-6-(5-chloro-2-methoxyphenyl)-2-methylpyrimidine

HRID 28556

Reaction equation

HRID 28556 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8]2[N:13]=[C:12]([CH3:14])[NH:11][C:10](=O)[CH:9]=2)[CH:7]=1.CN(C)C=O.C(Cl)(=O)C([Cl:26])=O>ClCCl.O1CCOCC1>[Cl:26][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])[N:13]=[C:12]([CH3:14])[N:11]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1363418886-(5-Chloro-2-methoxyphenyl)-2-methylpyrimidin-4-ol

Product 1

HCID 656453264-Chloro-6-(5-chloro-2-methoxyphenyl)-2-methylpyrimidineYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one (520 mg, 2.1 mmol) in dichloromethane (20 ml) and 1,4-dioxane (20 ml) was added N,N-dimethylformamide (0.2 ml) followed by a solution of oxalyl chloride in dichloromethane (2 M, 4.2 ml). After stirring for 1 hour, the mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (60 ml). The organic phase was dried over magnesium sulfate and concentrated under vacuum to give 4-chloro-6-(5-chloro-2-methoxy-phenyl)-2-methyl-pyrimidine (530 mg, 94% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.67 (s, 3H, CH3), 3.91 (s, 3H, CH3), 7.26 (d, 1H, J=9.2 Hz, Ar), 7.59 (dd, 1H, J=8.8 Hz, J=2.6 Hz, Ar), 7.95 (s, 1H, Ar), 7.96 (d, 1H, J=2.9 Hz, Ar).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (60 ml)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4749b9b34d4d42a3a1c43ccca0c7b463
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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