Ethyl orthoformate → 6-chloro-1H-pyrido[3,2-d]pyrimidin-4-one

HRID 1182933Notes

Reaction equation

HRID 1182933 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[CH:12](OCC)(OCC)OCC>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][CH:12]=[N:11][C:9](=[O:10])[C:3]=2[N:4]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 107497043-Amino-6-chloropyridine-2-carboxamide

Product 1

HCID 1785182176-chloro-1H-pyrido[3,2-d]pyrimidin-4-oneYield 82%

Procedure

A suspension of 3-amino-6-chloropicolinamide (1.67 g, 9.74 mmol) in triethyl orthoformate (73.0 mL) was refluxed for 3 hours. The reaction mixture was cooled to room temperature, and then filtered. The filtercake was dried under vacuum to give 6-chloropyrido[3,2-d]pyrimidin-4(1H)-one (1.45 g, 82%) as a brown solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 7.66 (1H, d, J=8.4 Hz), 8.00 (1H, s), 8.03 (1H, d, J=1.2 Hz), 12.57 (1H, brs).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationfiltered
  3. customThe filtercake was dried under vacuum

Sources & evidence

ORD record
ord-8e03bba2f89c4b50a1c1c06eebc8b332
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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