Triphenylphosphine → 6-Methoxy-7-(3-methylsulphonylpropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 855736Notes

Reaction equation

HRID 855736 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](=[O:39])[N:26]([CH2:31][O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[CH:27]=[N:28]2)=[CH:23][C:22]=1[O:40][CH3:41].[CH3:42][S:43]([CH2:46][CH2:47][CH2:48]O)(=[O:45])=[O:44].CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[CH3:41][O:40][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:21]=1[O:20][CH2:48][CH2:47][CH2:46][S:43]([CH3:42])(=[O:45])=[O:44])[N:28]=[CH:27][N:26]([CH2:31][O:32][C:33](=[O:38])[C:34]([CH3:35])([CH3:36])[CH3:37])[C:25]2=[O:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2004243-(Methylsulfonyl)-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Product 1

HCID 220305896-Methoxy-7-(3-methylsulphonylpropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (8.9 g, 35.2 mmol) was added to a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (6 g, 19.6 mmol), (prepared as described for the starting material in Example 7), in methylene chloride (150 ml). This was followed by the addition of 3-methylsulphonylpropanol (3.5 g, 25.4 mmol) and diethylazodicarboxylate (5.55 ml, 35.2 mmol) in portions. The reaction was complete once the reaction became homogeneous. Silica was added and the volatiles were removed by evaporation. The free flowing powder was placed on the top of a flash chromatography column pre-equilibrated with ethyl acetate (100%). Elution was done using ethyl acetate (100%) followed by methylene chloride/ethyl acetate/methanol (60/35/3). The volatiles were removed by evaporation to give 6-methoxy-7-(3-methylsulphonylpropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (7.58 g, 91%) as a white solid.

Workup

  1. custom(prepared
  2. additionSilica was added
  3. customthe volatiles were removed by evaporation
  4. washElution
  5. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-ae7210b2f56048fd84448c2f9bd9fa33
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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