Tetrabutylammonium Fluoride → Pyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858307Notes

Reaction equation

HRID 1858307 reaction equation
[Si](OCCC1C=C([N:27]2[C:32]3=[N:33][C:34](NC4C=CC(OCCN(CC)CC)=CC=4)=[N:35][CH:36]=[C:31]3[CH2:30][N:29](C3C=CC(Cl)=CC=3Cl)[C:28]2=[O:60])C=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH:27]1[C:32]2=[N:33][CH:34]=[N:35][CH:36]=[C:31]2[CH:30]=[N:29][C:28]1=[O:60]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53662365HCID 53662365, compound

Product 1

HCID 11240565Pyrimido[4,5-d]pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 200 mg (0.23 mmol) of 1-[3-(tert-butyldiphenylsilyloxyethyl)phenyl]-3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 5 ml of tetrahydrofuran was treated with 0.5 ml (0.5 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. After 1 hour the mixture was evaporated and the product purified by chromatography on silica gel using dichloromethane/methanol in a ratio 20:1 as eluting solvent. Evaporation of the product-containing fractions followed by trituration of the residue with hexane and filtration gave 60 mg (42%) 3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-[3-(2-hydroxyethyl))phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 110° C.

Workup

  1. customAfter 1 hour the mixture was evaporated
  2. customthe product purified by chromatography on silica gel
  3. washas eluting solvent
  4. customEvaporation of the product-containing fractions
  5. filtrationfollowed by trituration of the residue with hexane and filtration

Sources & evidence

ORD record
ord-5f830118723a499b959abbb57c86d118
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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