Sodium Carbonate → 2-(2-Ethoxyphenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one

HRID 1936699Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[C:10]([C:18]([NH2:20])=[O:19])=[N:11][CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])=O)[CH3:2].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[Na].[Na].C(=O)([O-])[O-].[Na+].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]1[NH:20][C:18](=[O:19])[C:10]2[N:11]=[CH:12][CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:9]=2[N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 210 °C

Procedure

A mixture of 3-(2-ethoxybenzoylamino)-4-n-propylpyridine-2-carboxamide (Preparation 7; 1.52 g, 0.0046 mol) and anhydrous zinc chloride (1.88 g, 0.014 mol) was heated at 210° C. for 0.25 hour. The cool mixture was dissolved in methanol (20 ml) and this solution poured into an aqueous solution of disodium ethylenediamine tetraacetic acid (10.3 g in 200 ml water). The resulting mixture was basified with saturated aqueous sodium carbonate solution (20 ml), then extracted with dichloromethane (4×60 ml). The combined organic extracts were dried (MgSO4) and evaporated under vacuum, then the residue crystallized from ethyl acetate to give the title compound as a white solid (0.92 g, 65%), m.p. 134-137° C.

Workup

extractionextracted with dichloromethane (4×60 ml)
dry with materialThe combined organic extracts were dried (MgSO4)
customevaporated under vacuum
customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record: ord-bd1baab3f54d45e6bb0e10491f8d1d81
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391885B1

Reaction notes

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