Tetrabutylammonium Fluoride → HCID 22125175, compound

HRID 1858340Notes

Reaction equation

HRID 1858340 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([N:27]2[C:32]3=[N:33][C:34]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[N:35][CH:36]=[C:31]3[CH2:30][N:29]([CH2:44][C:45]3[O:46][CH:47]=[CH:48][CH:49]=3)[C:28]2=[O:50])[CH:24]=[CH:25][CH:26]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:46]1[CH:47]=[CH:48][CH:49]=[C:45]1[CH2:44][N:29]1[CH2:30][C:31]2[C:32](=[N:33][C:34]([NH:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[N:35][CH:36]=2)[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][OH:18])[CH:22]=2)[C:28]1=[O:50]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54169456HCID 54169456, compound

Product 1

HCID 22125175HCID 22125175, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 320 mg (0.47 mmol) of 1-[3-(2-tert-butyldiphenylsilyloxyethyl)-phenyl]-3-(furan-2-yl-methyl)-7-phenylamino-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one in dry tetrahydrofuran (5 ml) was treated with 0.6 ml (0.6 mmol) of tetrabutylammonium fluoride (1M solution in tetrahydrofuran) then stirred at room temperature for 2 hours. The solvent was evaporated and the crude material purified by flash chromatography on silica gel, eluting with 4:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 170 mg (82%) of 3-(furan-2-yl-methyl)-1-[3-(2-hydroxyethyl)-phenyl]-7-phenylamino-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one as a pale pink solid of melting point 195° C. [Mass spectrum (ESI) MH+ =442].

Workup

  1. customThe solvent was evaporated
  2. customthe crude material purified by flash chromatography on silica gel
  3. washeluting with 4:1 ethyl acetate/hexane
  4. additionProduct containing fractions
  5. customevaporated

Sources & evidence

ORD record
ord-633cb59852114b4fb84fbfc5d2611eb8
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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