Diphenyl Ether → 2,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine

HRID 543120Notes

Reaction equation

HRID 543120 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:4]=1[CH2:5][CH:6]([C:12]([CH3:14])=O)[C:7]([O:9]CC)=O.[NH2:21][C:22]1[N:27]=[C:26]([NH2:28])[CH:25]=[C:24]([NH2:29])[N:23]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>O.C(O)C>[NH2:21][C:22]1[N:23]=[C:24]([NH2:29])[C:25]2[C:12]([CH3:14])=[C:6]([CH2:5][C:4]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:3]=3[O:2][CH3:1])[C:7](=[O:9])[NH:28][C:26]=2[N:27]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 138632,4,6-TriaminopyrimidineHCID 12597482Ethyl alpha-(2,5-dimethoxybenzyl)acetoacetate

Product 1

HCID 125974832,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidineYield 65.8%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of ethyl α-(2,5-dimethoxybenzyl)acetoacetate (21.2 g), 2,4,6-triaminopyrimidine (10 g) and diphenyl ether (100 ml) was heated at 190°-230° C. for 1.5 hours in an apparatus fitted with a Dean-Stark trap and water-ethanol (4 ml) was collected. Methanol (200 ml) and ethanel (50 ml) were added to the cooled reaction mixture. The resulting solid was collected by filtration and treated with boiling water (1 l) to give 2,4-diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido [2,3-d]pyrimidine (17 g), m.p. 325°-326° C.

Workup

  1. temperaturewas heated at 190°-230° C. for 1.5 hours in an apparatus
  2. customwas collected
  3. additionMethanol (200 ml) and ethanel (50 ml) were added to the cooled reaction mixture
  4. filtrationThe resulting solid was collected by filtration
  5. additiontreated with boiling water (1 l)

Sources & evidence

ORD record
ord-281bb03f444f4fce94e64c9b61c5179e
Source dataset
uspto-grants-1987_04
Patent number
US04661490

Reaction notes

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