Ethanol → HCID 178467012, compound

HRID 536064Notes

Reaction equation

HRID 536064 reaction equation
CC(C)(C)C(OC[N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[CH:13][C:14]=2[OH:18])[N:9]=[CH:8]1)=O.[C:23]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:24]=1.C(O)C.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.CO>C(Cl)Cl.N>[CH2:23]([O:18][C:14]1[CH:13]=[C:12]([O:19][CH3:20])[CH:11]=[C:10]2[C:15]=1[C:16](=[O:17])[N:7]=[CH:8][NH:9]2)[CH3:24]

Participants

9

Reactant 6

HCID 702EthanolHCID 887MethanolHCID 1140TolueneHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 119745575-Hydroxy-7-methoxy-3-pivaloyloxymethyl-quinazolin-4-one

Product 1

HCID 178467012HCID 178467012, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of [5-hydroxy-7-(methyloxy)-4-oxo-3(4H)-quinazolinyl]methyl 2,2-dimethylpropanoate (1 g, 3.26 mmol, prepared according to J. Med. Chem. (2006) 49 6465), triphenylphosphine (1.370 g, 5.22 mmol), and ethanol (0.210 mL, 3.59 mmol) in DCM (10 mL) at 0° C. was treated dropwise over 2 minutes with a 40% solution of DEAD in toluene (2.379 mL, 5.22 mmol). After addition, the mixture was warmed to room temperature and stirred for 3 hours before being concentrated. The residue was dissolved in 7 M ammonia in methanol (10 mL, 70.0 mmol) and the mixture was stirred for 3 days. The solid was collected by filtration and washed with MeOH and CH2Cl2 to give 5-(ethyloxy)-7-(methyloxy)-4(1H)-quinazolinone (286 mg, 40%) as a white solid. MS (m/z) 221.1 (M+H+).

Workup

  1. additionAfter addition
  2. concentrationbefore being concentrated
  3. stirringthe mixture was stirred for 3 days
  4. filtrationThe solid was collected by filtration
  5. washwashed with MeOH and CH2Cl2

Sources & evidence

ORD record
ord-19f756f0445e4cfaa394c0d9abffc6be
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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