Ethyl orthoformate → 5-Chloropyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1805763Notes

Reaction equation

HRID 1805763 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4](Cl)[CH:3]=1.[CH:13](OCC)(OCC)OCC>>[Cl:11][C:6]1[C:7]2[C:8](=[O:9])[NH:10][CH:13]=[N:1][C:2]=2[CH:3]=[CH:4][N:5]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 580930524-Amino-2,6-dichloronicotinamide

Product 1

HCID 1361111785-Chloropyrido[4,3-d]pyrimidin-4(3H)-one

Procedure

A suspension mixture of 4-amino-2,6-dichloronicotinamide (1.12 g, 6.53 mmol) and triethyl orthoformate (20 mL, 17.8 g, 120.3 mmol) was heated at 150° C. for 6 hours in a Teflon screwed pressure vessel. After it was cooled to room temperature, evaporation of triethyl orthoformate afforded crude product that was crystallized from a mixed solvent of toluene and methanol to afford product the title compound. 1H NMR (DMSO-d6) 7.55 (d, J=5.6 Hz, 1H), 8.30 (s, 1H), 8.55 (d, J=5.6 Hz, 1H), 12.72 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 116.4, 121.0, 149.9, 150.9, 151.4, 157.6, 158.0; ESI-MS m/z 181.0 (MH+).

Workup

  1. customevaporation of triethyl orthoformate
  2. customafforded crude product that
  3. customwas crystallized from a mixed solvent of toluene and methanol

Sources & evidence

ORD record
ord-89ef53b0df7943b4b4bbd8ee8415669e
Source dataset
uspto-grants-2013_01
Patent number
US08354526B2

Reaction notes

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