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Sodium hydride → 2-(3-Bromo-5-methylphenyl)-2-(5-isopropyl-2,6-dimethoxypyrimidin-4-YL)acetonitrile

HRID 2194746
Notes
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Reaction equation

HRID 2194746 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.[Br: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>[Br: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 236288332-(3-Bromo-5-methylphenyl)acetonitrile

Product 1

HCID 596868362-(3-Bromo-5-methylphenyl)-2-(5-isopropyl-2,6-dimethoxypyrimidin-4-YL)acetonitrileYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (47.63 g, 0.22 M) and (3-bromo-5-methyl-phenyl)-acetonitrile (42 g, 0.2 M) in anhydrous DMF (220 mL) in an ice-water bath under an atmosphere of nitrogen, was added 60% sodium hydride (16 g, 0.4 M) in portions. 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, ether:hexanes (1:7)) to afford 68 g (87%) of a white solid. m.p. 123-124° C.; 1H NMR (200 MHz, CDCl3) δ 1.11 (3H, d, J=6.9 Hz), 1.15 (3H, D, J=6.9 Hz), 2.32 (3H, s), 2.97 (1H, m), 4.00 (3H, s), 4.01 (3H, s), 5.34 (1H, s), 7.14 (1H, s), 7.28 (1H, s), 7.31 (1H, s).

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, ether:hexanes (1:7))

Sources & evidence

ORD record
ord-4ae93b524a0f46099366f6b071c7f368
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08334295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes