2-Methoxyethylamine → 7,8-dihydro-5-hydroxy-N,8-bis(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxamide

HRID 225347Notes

Reaction equation

HRID 225347 reaction equation
C(O[C:4]([C:6]1[C:21](=[O:22])[N:20]([CH2:23][CH2:24][O:25][CH3:26])[C:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:13][C:8]=2[C:7]=1[OH:27])=[O:5])C.[CH3:28][O:29][CH2:30][CH2:31][NH2:32]>C(O)C>[OH:27][C:7]1[C:8]2[CH:13]=[N:12][C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:10][C:9]=2[N:32]([CH2:31][CH2:30][O:29][CH3:28])[C:4](=[O:5])[C:6]=1[C:21]([NH:20][CH2:23][CH2:24][O:25][CH3:26])=[O:22]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 54727901Ethyl 5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 547245707,8-dihydro-5-hydroxy-N,8-bis(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.0 g. (0.0027 mole) of 7,8-dihydro-5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (prepared as in Example 9) was added 0.4 g. (0.0054 mole) of 2-methoxyethylamine in 25 ml. of ethanol and this was heated at reflux for 4 hours. The reaction was then filtered and chilled and the filtrate gave up a solid that was collected on a suction filter and rinsed with petroleum ether. No further purification was necessary--m.p. 150°-154° C.

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationThe reaction was then filtered
  3. temperaturechilled
  4. customthe filtrate gave up a solid
  5. customthat was collected on a suction
  6. filtrationfilter
  7. washrinsed with petroleum ether
  8. customNo further purification

Sources & evidence

ORD record
ord-5036cea1a418490b89950f0a932dcd40
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

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