HCID 58930947, compound → HCID 58931397, compound

HRID 853568Notes

Reaction equation

HRID 853568 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:18]3[N:19]=[CH:20][N:21]=[C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][CH:34]5[CH2:36][CH2:35]5)=[O:32])=[C:26]([F:37])[CH:25]=4)[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.O1CCCC1.[Pt]=O>[CH:34]1([NH:33][C:31]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][C:22]3[C:17]4[CH:16]=[C:15]([C:12]5[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=5)[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:45])([CH3:44])[CH3:46])[C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:25][C:26]=2[F:37])=[O:32])[CH2:36][CH2:35]1

Participants

5

Reactant 1

HCID 58930947HCID 58930947, compound

Product 1

HCID 58931397HCID 58931397, compoundYield 70.8%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 263 mg of 1-(4-(6-(4-benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-2-fluorophenyl)-3-cyclopropylurea in 7 ml of ethanol and 3 ml of tetrahydrofuran, 30 mg of platinum oxide was added and the mixture was stirred overnight at room temperature and ordinary pressure under a hydrogen atmosphere, after which it was filtered with celite and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate) to obtain 160 mg of the title compound.

Workup

  1. additionwas added
  2. filtrationordinary pressure under a hydrogen atmosphere, after which it was filtered with celite and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44aa9871f1204acba74f6bc5da6fde77
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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