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

HRID 372998Notes

Reaction equation

HRID 372998 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 recrystallised 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 recrystallised from ethanol

Sources & evidence

ORD record
ord-e5ef1ee8fa57457580765a4dcf39d892
Source dataset
uspto-grants-1992_11
Patent number
US05162316

Reaction notes

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