Ethyl orthoformate → 7-(trifluoromethyl)pyrido[3,2-d]pyrimidin-4(3H)-one

HRID 627721Notes

Reaction equation

HRID 627721 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([NH2:14])=[O:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:15](OCC)(OCC)OCC>>[F:10][C:8]([F:11])([F:9])[C:6]1[CH:5]=[N:4][C:3]2[C:12](=[O:13])[NH:14][CH:15]=[N:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 867281563-Amino-5-(trifluoromethyl)picolinamide

Product 1

HCID 1357416507-(trifluoromethyl)pyrido[3,2-d]pyrimidin-4(3H)-oneYield 84%

Conditions

Temperature
120 °C

Procedure

A vial was charged with 3-amino-5-(trifluoromethyl)picolinamide (615 mg, 3.00 mmol) and triethyl orthoformate (2496 μl, 14.99 mmol). The vial was sealed and the mixture was heated at 120° C. for 17 h. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with heptane. 7-(trifluoromethyl)pyrido[3,2-d]pyrimidin-4(3H)-one (540 mg, 2.51 mmol, 84% yield) was isolated as a tan solid. LC/MS (ESI) m/z=216.0 (M+H).

Workup

  1. customThe vial was sealed
  2. temperatureUpon cooling
  3. filtrationthe heterogeneous mixture was filtered
  4. washthe solids were washed with heptane

Sources & evidence

ORD record
ord-8eafaf9f7c5243cabd304f18f72d432b
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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