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Sodium hydride → (5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanone

HRID 426185
Notes
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Reaction equation

HRID 426185 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([CH:15]([C:18]2[C:23]([CH2:24][CH3:25])=[C:22]([O:26][CH3:27])[N:21]=[C:20]([O:28][CH3:29])[N:19]=2)C#N)[CH:11]=[C:12]([CH3:14])[CH:13]=1)(C)(C)C.[H-].[Na+].O.C1(C)C=CC(S(O)(=O)=[O:42])=CC=1>CN(C=O)C.CO>[CH2:24]([C:23]1[C:18]([C:15]([C:10]2[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH2:7][OH:6])[CH:9]=2)=[O:42])=[N:19][C:20]([O:28][CH3:29])=[N:21][C:22]=1[O:26][CH3:27])[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 178437280HCID 178437280, compound

Product 1

HCID 59184675(5-Ethyl-2,6-dimethoxy-pyrimidin-4-yl)-(3-hydroxymethyl-5-methyl-phenyl)-methanoneYield 628.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

To a stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-phenyl]-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile (3.74 g, 8.47 mmol) in anhydrous DMF (40 ml), was added 60% sodium hydride (373 mg, 9.32 mmol). After 20 min., oxygen was bubbled into the reaction mixture for 3 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was stirred with p-toluenesulfonic acid monohydrate (152 mg, 0.8 mmol) in methanol (10 ml) for 2 hr. at room temperature. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 3:2)) to afford 1.59 g (59%) of a white solid. m.p. 101-103° C.; 1H NMR (200 MHz, CDCl3) δ 1.05 (3H, t, J=7.4 Hz), 2.35-2.48 (5H, m), 3.93 (3H, s), 4.06 (3H, s), 4.63 (2H, br. S), 7.40 (1H, s), 7.56 (1H, s), 7.60 (1H, s).

Workup

  1. customoxygen was bubbled into the reaction mixture for 3 hr
  2. customThe mixture was partitioned between ether and aqueous saturated ammonium chloride solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customat room temperature
  8. customThe mixture was evaporated in vacuo
  9. customthe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 3:2))

Sources & evidence

ORD record
ord-f665b91ca31842808c998b0bf45f5ae2
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