Sodium hydride → HCID 70937836, compound

HRID 1503274Notes

Reaction equation

HRID 1503274 reaction equation
[CH3:1][N:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][CH:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:3]1=[O:19].[H-].[Na+].Cl[C:23]1[N:28]=[CH:27][C:26]([C:29]#[C:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][N:24]=1>CN(C=O)C>[CH3:1][N:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([C:23]2[N:24]=[CH:25][C:26]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][N:28]=2)([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:3]1=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70925639HCID 70925639, compoundHCID 86673011HCID 86673011, compound

Product 1

HCID 70937836HCID 70937836, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (RS)-benzyl 1,5,5-trimethyl-2-oxopyrrolidine-3-carboxylate (206 mg, 787 μmol) in 4 ml of dry DMF was purged with argon and cooled to 0° C. Then a 60% suspension of sodium hydride (31.5 mg, 0.79 mmol) was added and the mixture was stirred for 40 min at room temperature whereby a white suspension was formed. Then 2-chloro-5-(phenylethynyl)pyrimidine (CAS: [1051388-40-9]) (130 mg, 606 μmol) was added, the mixture was stirred for 30 min at 80° C., and then quenched by addition of 1 ml of saturated ammonium chloride solution. After extraction with ethyl acetate/water, drying over sodium sulfate and concentration; the residue (440 mg, yellow oil) was taken up in ethyl acetate, adsorbed onto 3 g of silicagel and loaded onto a 20 g prepacked flash chromatography column. After elution with a 10% to 60% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 212 mg (80%) of the title compound as a light yellow waxy solid, MS: m/e=440.3 (M+H+).

Workup

  1. customwas formed
  2. stirringthe mixture was stirred for 30 min at 80° C.
  3. customquenched by addition of 1 ml of saturated ammonium chloride solution
  4. extractionAfter extraction with ethyl acetate/water
  5. dry with materialdrying over sodium sulfate and concentration
  6. washAfter elution with a 10% to 60% ethyl acetate in heptane gradient
  7. additionthe fractions containing the desired product
  8. customwere collected

Sources & evidence

ORD record
ord-248f95eace144b31bbda1f98a06a5975
Source dataset
uspto-grants-2015_12
Patent number
US09212171B2

Reaction notes

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