Trimethyl orthoformate → 2-Chloro-4-(3-dimethoxymethyl-phenyl)-pyrimidine

HRID 14783

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)C=O)[CH:5]=[CH:4][N:3]=1.Cl.O1CCOCC1.[CH3:23][O:24][CH:25](OC)[O:26][CH3:27]>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:13]=[C:14]([CH:25]([O:26][CH3:27])[O:24][CH3:23])[CH:15]=2)[CH:5]=[CH:4][N:3]=1

Participants

Reactant 3

HCID 9005Trimethyl orthoformate

HCID 204431481,4-Dioxane hydrochloride

HCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehyde

Product 1

HCID 866032612-Chloro-4-(3-dimethoxymethyl-phenyl)-pyrimidine

Procedure

Intermediate 1 (3.69 g) was refluxed for two hours in trimethylorthoformate containing 10 mL of 4N HCl/dioxane. The solvent was removed by rotary evaporation to give product, which showed the expected M+H+ of 265 by LC-MS.

Workup

customThe solvent was removed by rotary evaporation
customto give product, which

Sources & evidence

ORD record: ord-7533bb8fdece41aa9e7946c5e94b613b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Linked notes

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