Triphenylphosphine → 6-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

HRID 634753Notes

Reaction equation

HRID 634753 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]1.O[C:24]1[CH:33]=[C:32]2[C:27]([C:28](=[O:42])[N:29]([CH2:34][O:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[CH:30]=[N:31]2)=[CH:26][C:25]=1[O:43][CH3:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:44][O:43][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:24]=1[O:22][CH2:21][CH2:20][CH2:19][N:16]1[CH2:17][CH2:18][O:13][CH2:14][CH2:15]1)[N:31]=[CH:30][N:29]([CH2:34][O:35][C:36](=[O:41])[C:37]([CH3:38])([CH3:39])[CH3:40])[C:28]2=[O:42]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1995763-Morpholino-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Product 1

HCID 227322766-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-oneYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (2.67 ml, 17 mmol) was added dropwise to a solution of 3-morpholinopropan-1-ol (1.54 g, 10 mmol), 7-hydroxy-3,4-dihydro-6-methoxy-3-((pivaloyloxy)methyl)quinazolin-4-one (2.6 g, 8.5 mmol) and triphenylphosphine (4.45 g, 17 mmol) in methylene chloride (40 ml). After stirring for 2 hours at ambient temperature, the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (97/3 followed by 95/5) to give 3,4-dihydro-6-methoxy-3-((pivaloyloxy)metyl)-7-(3-morpholinopropoxy)quinazolin-4-one (3.6 g, 97%).

Workup

  1. customthe volatiles were removed by evaporation
  2. customThe residue was purified by column chromatography
  3. washeluting with methylene chloride/methanol (97/3 followed by 95/5)

Sources & evidence

ORD record
ord-33bfcf35bf734b52b59d70aa5d195f4f
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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