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Sodium hydride → (3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

HRID 426124
Notes
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Reaction equation

HRID 426124 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:23][C:24]#[N:25])[CH:19]=[C:20]([CH3:22])[CH:21]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:23]([C:2]2[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=2)[C:24]#[N:25])[CH:19]=[C:20]([CH3:22])[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 226001322-(3-Chloro-5-methylphenyl)acetonitrile

Product 1

HCID 59184692(3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrileYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-Chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (23.8 g, 0.11 mol) and (3-Chloro-5-methyl-phenyl)-acetonitrile (47) (16.6 g, 0.1 mol) in anhydrous DMF (200 ml) in an ice-water bath under an atmosphere of nitrogen, was portionwise added 60% sodium hydride (8.8 g, 0.22 mol). After stirring for 1 hr, the mixture was stirred at room temperature for overnight. The mixture was neutralized with aqueous saturated ammonium chloride solution. The crude product was extracted with ether and purified by silica gel column chromatography (eluent, EA:hexane (1:10)) to afford 24 g (69%) of a white solid. m.p. 105-106° C.; 1H NMR (200 MHz, CDCl3) δ: 1.11 (3H, d, J=7.1 Hz), 1.15 (3H, d, J=7.1 Hz), 2.32 (3H, s), 3.00 (1H, m), 4.00 (3H, s), 4.02 (3H, s), 5.33 (1H, s), 7.10-7.16 (3H, m).

Workup

  1. stirringthe mixture was stirred at room temperature for overnight
  2. extractionThe crude product was extracted with ether
  3. custompurified by silica gel column chromatography (eluent, EA:hexane (1:10))

Sources & evidence

ORD record
ord-9ae18f6bde354fa5ae6461ca533cda45
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106064B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes