Ethyl orthoformate → 7-chloro-1H-pyrido[3,2-d]pyrimidin-4-one

HRID 930450Notes

Reaction equation

HRID 930450 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:12](OCC)(OCC)OCC>>[Cl:8][C:6]1[CH:5]=[N:4][C:3]2[C:9](=[O:10])[N:11]=[CH:12][NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 218200583-Amino-5-chloropyridine-2-carboxamide

Product 1

HCID 1785182197-chloro-1H-pyrido[3,2-d]pyrimidin-4-oneYield 88.5%

Conditions

Temperature
155 °C

Procedure

A suspension of 3-amino-5-chloropicolinamide (1.1 g, 6.41 mmol) in triethyl orthoformate (15.99 mL, 96 mmol) was stirred at 155° C. for 22 hours. After cooling to RT, the yellow precipitate was collected by vacuum filtration and washed with hexanes to yield the title intermediate (1.03 g, 5.67 mmol) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.20 (s, 1 H) 8.27 (d, J=2.35 Hz, 1 H) 8.80 (d, J=2.25 Hz, 1 H) 12.68 (br. s., 1 H). LC/MS (ESI+) m/z=182 (M+H).

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe yellow precipitate was collected by vacuum filtration
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-bd7124b4ca314ec78c1b96449f87b864
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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