Water → 5-Amino-7,8-dihydro-8-(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 225346Notes

Reaction equation

HRID 225346 reaction equation
[C:1]([C:3]1[C:4]([NH:15][CH2:16][CH2:17][O:18][CH3:19])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1)#[N:2].[CH2:20]([O:22]CC)[CH3:21].C([CH:27]([C:31](Cl)=[O:32])[C:28](Cl)=[O:29])C.O>C(O)C.C(O)(=O)C>[CH2:20]([O:22][C:31]([C:27]1[C:28](=[O:29])[N:15]([CH2:16][CH2:17][O:18][CH3:19])[C:4]2[N:5]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:7]=[CH:8][C:3]=2[C:1]=1[NH2:2])=[O:32])[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 109209242-Ethylpropanedioyl dichlorideHCID 127840885-Cyano-4-(2-methoxyethylamino)-2-phenyl pyrimidine

Product 1

HCID 127841045-Amino-7,8-dihydro-8-(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To 9.3 g. (0.037 mole) of 5-cyano-4-(2-methoxyethylamino)-2-phenyl pyrimidine in 350 ml. of diethyl ether was added 2.8 g. (0.019 mole) of ethyl malonyl chloride and this mixture was stirred at room temperature for 4.5 hours. Then the solid material was filtered off and the filtrate evaporated to dryness. Ethanol was added until a solution was obtained and this solution was added to 0.85 g. (0.057 mole) of Na in ethanol and stirred 20 minutes. A little water was added and the solution was acidified with acetic acid. The solid product was collected on a suction filter and recrystallized from ethanol to give 2.0 g. of product--m.p. 245°-247° C.

Workup

  1. filtrationThen the solid material was filtered off
  2. customthe filtrate evaporated to dryness
  3. additionEthanol was added until a solution
  4. customwas obtained
  5. additionthis solution was added to 0.85 g
  6. customThe solid product was collected on a suction
  7. filtrationfilter
  8. customrecrystallized from ethanol
  9. customto give 2.0 g

Sources & evidence

ORD record
ord-4e9dfcb5d98f42cb9b8a4821573491ee
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

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