Water → HCID 13458455, compound

HRID 1981150Notes

Reaction equation

HRID 1981150 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:6][CH:7]([C:13]([CH3:15])=O)[C:8]([O:10]CC)=O.[NH2:21][C:22]1[N:27]=[C:26]([NH2:28])[CH:25]=[C:24]([NH2:29])[N:23]=1.O>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH2:21][C:22]1[N:23]=[C:24]([NH2:29])[C:25]2[C:13]([CH3:15])=[C:7]([CH2:6][C:5]3[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:8](=[O:10])[NH:28][C:26]=2[N:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 138632,4,6-TriaminopyrimidineHCID 12217345HCID 12217345, compound2×

Product 1

HCID 13458455HCID 13458455, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A mixture of ethyl α-(3,4-dimethoxybenzyl)acetoacetate (42 g) and 2,4,6-triaminopyrimidine (21 g) in diphenyl ether (120 ml) was heated at 190°-230° C. for 2 hours during which time the ethanol and water formed were azeotropically removed. The reaction was cooled, and methanol (250 ml) and ethanol (50 ml) were added. The resulting solid was collected by filtration and treated with boiling water (1) to give 2,4-diamino-5-methyl-6-(3,4-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine (26 g), m.p. 346°-348° C.

Workup

  1. customformed
  2. customwere azeotropically removed
  3. temperatureThe reaction was cooled
  4. additionmethanol (250 ml) and ethanol (50 ml) were added
  5. filtrationThe resulting solid was collected by filtration
  6. additiontreated with boiling water (1)

Sources & evidence

ORD record
ord-9aed0cd60b4c48c3a758f8ba2611a09c
Source dataset
uspto-grants-1985_04
Patent number
US04512992

Reaction notes

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