Isopropanol → [7-(benzyloxy)-5-isopropoxy-4-oxoquinazolin-3(4H)-yl]methyl pivalate

HRID 639979Notes

Reaction equation

[CH:1](O)([CH3:3])[CH3:2].[C:5]([O:11][CH2:12][N:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][C:20]=2[OH:24])[N:15]=[CH:14]1)(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>ClCCl>[C:5]([O:11][CH2:12][N:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][C:20]=2[O:24][CH:1]([CH3:3])[CH3:2])[N:15]=[CH:14]1)(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Isopropanol (1.5 ml, 18.7 mmol) was added to a solution of [7-(benzyloxy)-5-hydroxy-4-oxoquinazolin-3(4H)-yl]methyl pivalate (see WO01/094341, 6.5 g, 17.0 mmol) and triphenylphosphine (6.2 g, 23.8 mmol) in dichloromethane (300 ml). The reaction mixture was cooled to 0° C. and then a solution of di-tert-butylazodicarboxylate (4.7 g, 20.4 mmol) in dichloromethane (25 ml) was added dropwise over 30 minutes. The mixture was allowed to warm to room temperature and then stirred for 2 hours. The mixture was evaporated under reduced pressure to afford crude [7-(benzyloxy)-5-isopropoxy-4-oxoquinazolin-3(4H)-yl]methyl pivalate which was used in the next stage without further purification.

Workup

temperatureto warm to room temperature
customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record: ord-a4c7d538fe784cdab6ba7041f3d71357
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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