Triethylamine → HCID 135670773, compound

HRID 1936673Notes

Reaction equation

HRID 1936673 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.[F:27][C:28]([F:32])([F:31])[CH2:29][NH2:30].C(N(CC)CC)C>ClCCl>[F:27][C:28]([F:32])([F:31])[CH2:29][NH:30][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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 1356707527-Methylsulphonyl-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 135670773HCID 135670773, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-methylsulphonyl-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (0.72 g), 2,2,2-trifluoroethylamine hydrochloride (0.97 g) and triethylamine (0.73 g) in dichloromethane (15 ml) was stirred at ambient temperature for 48 hours and allowed to stand for 4 days. A yellow solid had formed which was collected by filtration and washed with dichloromethane. The filtrate was washed with dilute hydrochloric acid (15 ml) then water (10 ml) and the aqueous layers extracted with dichloromethane (2×7.5 ml). The combined organic layers were dried (magnesium sulphate) and evaporated under reduced pressure to yield a crude product. This was eluted from a silica column with diethyl ether:chloroform (4:1) and the combined fractions containing product were evaporated under reduced pressure to yield a residue which was recrystallized from isopropanol to yield the title compound, 0.13 g, m.p. 214-215.5° C.

Workup

  1. customA yellow solid had formed which
  2. filtrationwas collected by filtration
  3. washwashed with dichloromethane
  4. washThe filtrate was washed with dilute hydrochloric acid (15 ml)
  5. extractionwater (10 ml) and the aqueous layers extracted with dichloromethane (2×7.5 ml)
  6. dry with materialThe combined organic layers were dried (magnesium sulphate)
  7. customevaporated under reduced pressure
  8. customto yield a crude product
  9. washThis was eluted from a silica column with diethyl ether:chloroform (4:1)
  10. additionthe combined fractions containing product
  11. customwere evaporated under reduced pressure
  12. customto yield a residue which
  13. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-5b6579fa9da14366b00272a9cc86aba3
Source dataset
uspto-grants-2002_05
Patent number
US06391885B1

Reaction notes

Loading…