Triphenylphosphine → 7-(3-Morpholinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1386320Notes

Reaction equation

HRID 1386320 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O[CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]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>[O:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][CH2:22][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:20])[N:7]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH:8]=[N:9]3)=[CH:4][CH:3]=2)[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1995763-Morpholino-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 216992947-Hydroxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 216992697-(3-Morpholinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Hydroxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (750 mg, 2.7 mmol) was suspended in methylene chloride (40 ml) at 5° C. and 4-(3-hydroxypropyl)morpholine (490 mg, 3.4 mmol) and triphenylphosphine (890 mg, 3.4 mmol) were added. The mixture was stirred for 5 minutes and diethyl azodicarboxylate (590 mg, 3.4 mmol) was added over 5 minutes at 5° C. The reaction mixture was stirred at 5° C. for 30 minutes then at ambient temperature for 1 hour. The solution was then purified directly by column flash chromatography eluting with methylene chloride, and then ethyl acetate, acetonitrile/ethyl acetate (20/80), and acetonitrile/ethyl acetate/ammonia (50/50/0.5). The purified product was triturated with ether/isohexane and collected by filtration to give 7-(3-morpholinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (745 mg, 68%).

Workup

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

Sources & evidence

ORD record
ord-0ce57726cc7c4e3589fa07c15fa017e6
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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