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Ethyl Acetate → (5-Cyclopropyl-2,6-dimethoxy-pyrimidin-4-yl)-(3,5-dimethyl-phenyl)-acetonitrile

HRID 426252
Notes
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Reaction equation

HRID 426252 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:7]#N)#[N:2].Cl[C:14]1[C:19]([CH:20]2[CH2:22][CH2:21]2)=[C:18]([O:23][CH3:24])[N:17]=[C:16]([O:25][CH3:26])[N:15]=1.[H-].[Na+].C(OCC)(=O)C>CN(C=O)C>[CH:20]1([C:19]2[C:14]([CH:3]([C:4]3[CH:11]=[C:10]([CH3:12])[CH:9]=[C:6]([CH3:7])[CH:5]=3)[C:1]#[N:2])=[N:15][C:16]([O:25][CH3:26])=[N:17][C:18]=2[O:23][CH3:24])[CH2:22][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 591847574-Chloro-5-cyclopropyl-2,6-dimethoxy-pyrimidineHCID 667054463-(Cyanomethyl)-5-methylbenzonitrile

Product 1

HCID 66705526(5-Cyclopropyl-2,6-dimethoxy-pyrimidin-4-yl)-(3,5-dimethyl-phenyl)-acetonitrileYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Cyanomethyl-5-methyl-benzonitrile (97 mg, 0.621 mmol) and 4-chloro-5-cyclopropyl-2,6-dimethoxy-pyrimidine (140 mg, 0.652 mmol, 1.05 eq.) were dissolved in 2 mL DMF. Cool the reaction flask to 0° C. NaH (60%, 51 mg, 1.24 mmol, 2 eq.) was added portionwise at 0° C. The reaction was stirred at 0° C., then warmed up to room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) to give white solid (67 mg, 33%). LC-MS shows 335.2 (M+1). 1H NMR (300 MHz, CDCl3): δ 7.58 (s, 1H), 7.50 (s, 1H), 7.43 (s, 1H), 5.82 (s, 1H), 4.0 (d, 6H), 2.4 (s, 3H), 1.43 (m, 1H), 1.09 (m, 2H), 0.64 (m, 2H).

Workup

  1. temperaturewarmed up to room temperature for 2 hours
  2. washby washing with brine
  3. concentrationThe organic layer was concentrated down
  4. custompurified (silica gel, 0-50% EtOAC/hexane)

Sources & evidence

ORD record
ord-68eba562743d4049b002611ef04a3ffa
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106064B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes