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Sodium hydride → 5-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-isophthalonitrile

HRID 426278
Notes
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Reaction equation

HRID 426278 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[CH:7]=[C:8]([CH:11]=1)[C:9]#[N:10])#[N:2].Cl[C:15]1[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24][CH3:25])[N:18]=[C:17]([O:26][CH3:27])[N:16]=1.[H-].[Na+]>CN(C=O)C>[C:1]([CH:3]([C:15]1[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24][CH3:25])[N:18]=[C:17]([O:26][CH3:27])[N:16]=1)[C:4]1[CH:11]=[C:8]([C:9]#[N:10])[CH:7]=[C:6]([CH:5]=1)[C:12]#[N:13])#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 667055675-Cyanomethyl-isophthalonitrile

Product 1

HCID 591847545-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-isophthalonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

5-Cyanomethyl-isophthalonitrile (0.285 g, 1.70 mmol) and 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (0.360 g, 1.66 mmol) was dissolved in DMF (8.0 mL) and cooled to 0° C. 60% Sodium hydride (0.136 g, 3.40 mmol) was added portionwise and the reaction was stirred at 0° C. for 2 h, then rt overnight. The reaction was quenched with saturated ammonium chloride solution and pH was adjusted to ˜6.0 with 1N HCl. Mixture was extracted with ethyl acetate and organic layer was dried (MgSO4) and concentrated. The resulting residue was purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane) to give a white solid (0.2457 g, 43%). 1H NMR (300 MHz, CDCl3): δ 7.90 (s, 3H), 5.46 (s, 1H), 3.96 (s, 3H), 3.89 (s, 3H), 3.05-2.9 (m, 1H), 1.16 (d, J=6.9 Hz, 3H), 1.15 (d, J=7.2 Hz, 3H).

Workup

  1. customrt overnight
  2. customThe reaction was quenched with saturated ammonium chloride solution and pH
  3. extractionMixture was extracted with ethyl acetate and organic layer
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6fc24924f44c46e9b752ce10f90c2dc6
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