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Dimethylformamide → Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 606478
Notes
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Reaction equation

HRID 606478 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6][C:5]2=[O:17].C(OCC)(=O)C.[CH3:24][N:25](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6][C:5]2=[O:17])#[N:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 136014453Ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 136054489Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst

Conditions

Temperature
80 °C

Procedure

A suspension of ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate (2.00 g, 5.81 mmol), zinc cyanide (375 mg, 3.19 mmol) and tetrakis(triphenylphosphine)palladium (336 mg, 0.29 mmol) in DMF (10 mL) was stirred at 80° C. for 5 hr under argon atmosphere. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The precipitated solid was collected by filtration, washed with ethyl acetate, diisopropyl ether and water, dried over diphosphorus pentaoxide under reduced pressure to give the title compound as a pale-yellow powder (965 mg, 68%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with ethyl acetate, diisopropyl ether and water
  4. dry with materialdried over diphosphorus pentaoxide under reduced pressure

Sources & evidence

ORD record
ord-9df02a159c364311a50b8e63885e558e
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915267B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes