Triphenylphosphine → HCID 136090573, compound

HRID 1596281Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[NH:7][C:8]([C:12](=[O:18])[C:13]([CH3:17])([CH3:16])[CH2:14][CH3:15])=[N:9]2)=[CH:4][CH:3]=1.O[CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:12]([C:8]1[NH:7][C:6](=[O:19])[C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:3][CH:4]=2)[N:9]=1)=[O:18]

Participants

Conditions

Temperature: 5 °C

Procedure

7-hydroxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-one (750mg, 2.7 mmol) was suspended in methylene chloride (40 ml) and 4-(3-hydroxypropyl)morpholine (490 mg, 3.4 mmol) and triphenylphosphine (890 mg, 3.4 mmol) were added at 5° C. The mixture was stirred for 5 minutes at 5° C. and diethyl azodicarboxylate (590 mg, 3.4 mmol) was added over 5 minutes. The reaction mixture was stirred at 5° C. for 30 minutes then at ambient temperature for 1 hour. The reaction mixture was purified directly by column chromatography eluting with methylene chloride, then ethyl acetate, then acetonitrile/ethyl acetate (1/5), and finally acetonitrile/ethyl acetate/aqueous ammonia (50/50/0.5). The purified product was triturated with ether/isohexane and collected by filtration to give 3-methylpivaloyl-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (745 mg, 68%).

Workup

stirringThe reaction mixture was stirred at 5° C. for 30 minutes
waitat ambient temperature for 1 hour
customThe reaction mixture was purified directly by column chromatography
washeluting with methylene chloride
customThe purified product was triturated with ether/isohexane
filtrationcollected by filtration

Sources & evidence

ORD record: ord-53a63cba1b1548f38868177a2b105461
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291455B1

Reaction notes

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