Triethylamine → 7-(2-Ethoxycarbonylethylamino)-4-oxo-2-(2-propoxyphenyl)3,4-dihydropyrimido[4,5-d]pyrimidine

HRID 1936668Notes

Reaction equation

HRID 1936668 reaction equation
CS([C:5]1[N:10]=[C:9]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:23][CH2:24][CH3:25])[NH:13][C:14](=[O:15])[C:8]2=[CH:7][N:6]=1)(=O)=O.Cl.[CH2:27]([O:29][C:30](=[O:34])[CH2:31][CH2:32][NH2:33])[CH3:28].C(N(CC)CC)C>ClCCl>[CH2:27]([O:29][C:30]([CH2:31][CH2:32][NH:33][C:5]1[N:10]=[C:9]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:23][CH2:24][CH3:25])[NH:13][C:14](=[O:15])[C:8]2=[CH:7][N:6]=1)=[O:34])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 1356707527-Methylsulphonyl-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 1356707717-(2-Ethoxycarbonylethylamino)-4-oxo-2-(2-propoxyphenyl)3,4-dihydropyrimido[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-methylsulphonyl-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (1.0 g), β-alanine ethyl ester hydrochloride (1.10 g) and triethylamine (0.73 g) in dichloromethane (20 ml) was stirred at ambient temperature for 2.5 hours. The reaction mixture was extracted with dilute hydrochloric acid (20 ml) then water (10 ml), and the extracts back washed with dichloromethane (10 ml). The combined organic extracts were dried (magnesium sulphate) and evaporated under reduced pressure to yield a crude product which was recrystallized from ethanol:water to yield the title compound, 0.83 g, m.p. 142-3° C.

Workup

  1. extractionThe reaction mixture was extracted with dilute hydrochloric acid (20 ml)
  2. washwater (10 ml), and the extracts back washed with dichloromethane (10 ml)
  3. dry with materialThe combined organic extracts were dried (magnesium sulphate)
  4. customevaporated under reduced pressure
  5. customto yield a crude product which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c3f51564d3eb4165b3efa02e5c50c709
Source dataset
uspto-grants-2002_05
Patent number
US06391885B1

Reaction notes

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