Ethanol → [2-(6-Methoxy-quinazolin-4-yl)-ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1354206Notes

Reaction equation

HRID 1354206 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[C:13]#[C:14][C:15]1([OH:25])[CH2:24]CC2(OCCO2)CC1.[CH3:26][CH2:27][OH:28]>C1COCC1.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[CH2:13][CH2:14][CH:15]1[CH2:24][O:28][C:27]2([CH2:11][CH2:12][CH:3]([OH:2])[CH2:4][CH2:26]2)[O:25]1

Participants

5

Reactant 2

HCID 702EthanolHCID 211046688-(6-Methoxy-quinazolin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol

Product 1

HCID 86603231[2-(6-Methoxy-quinazolin-4-yl)-ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Platinum oxide (0.46 g) was added to a solution of 8-(6-methoxy-quinazolin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol (0.96 g, 2.88 mmol) in EtOH (40 ml) and THF (10 ml), and hydrogenation was carried out under a hydrogen atmosphere (1 bar). The reaction mixture was stirred in the presence of activated carbon (5 g) and filtered. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc and then EtOAc:MeOH 9/1).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  3. customThe residue was purified by column chromatography on silica gel (EtOAc

Sources & evidence

ORD record
ord-5d443ac33af84a09a6b4388cf7724908
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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