4-Hydroxymethylpyridine → 6-Methoxy-3-((pivaloyloxy)methyl)-7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one

HRID 1386295Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:32])[N:19]([CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH:20]=[N:21]2)=[CH:16][C:15]=1[O:33][CH3:34].[N:35]1[CH:40]=[CH:39][C:38]([CH2:41]O)=[CH:37][CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:34][O:33][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:14]=1[O:13][CH2:41][C:38]1[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=1)[N:21]=[CH:20][N:19]([CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:28])([CH3:29])[CH3:30])[C:18]2=[O:32]

Participants

Conditions

Temperature: 5 °C

Procedure

Diethyl azodicarboxylate (348 mg, 2 mmol) was added dropwise to a suspension of 7-hydroxy-6-methoxy-3((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (457 mg, 1.5 mmol), (prepared as described for the starting material in Example 22), 4-pyridinemethanol (218 mg, 2 mmol), and triphenylphosphine (524 mg, 2 mmol) in methylene chloride (7 ml) at 5° C. The mixture was stirred for 10 minutes at 5° C. and then 1 hour at ambient temperature. The mixture was poured directly on to a silica column and eluted with methylene chloride/methanol (95/5) to give 6-methoxy-3-((pivaloyloxy)methyl)-7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (510 mg, 85%).

Workup

custom(prepared
customat 5° C
custom1 hour
customat ambient temperature
additionThe mixture was poured directly on to a silica column
washeluted with methylene chloride/methanol (95/5)

Sources & evidence

ORD record: ord-ef418504f9ee45d9b10532fe136d0785
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265411B1

Reaction notes

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