Ethyl Acetate → HCID 57531368, compound

HRID 1091934Notes

Reaction equation

HRID 1091934 reaction equation
ClC1[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH3:21])[N:5]=[C:4]([C:22]2[C:27]([CH2:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:30][CH3:31])[N:3]=1.CC([N:35](C)C)=O.[C-]#N.[K+].C([O-])(O)=O.[Na+].CCO[C:49]([CH3:51])=O>>[CH2:28]([C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:30][CH3:31])[C:22]=1[C:4]1[N:5]=[C:6]([C:21]#[N:35])[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][CH2:18][CH2:19]2)=[C:49]([CH3:51])[N:3]=1)[CH3:29]

Participants

6

Reactant 5

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 31374Dimethylacetamide2×HCID 516892Sodium BicarbonateHCID 57531455HCID 57531455, compound

Product 1

HCID 57531368HCID 57531368, compound

Conditions

Temperature
130 °C

Procedure

To a sealed tube containing [4-chloro-2-(2,6-diethyl-phenyl)-6-methyl-pyrimidin-5-ylmethyl]-methyl-(1S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine 9 (3.0 mL of a 0.2 M DMA solution, 0.6 mmol) is added KCN (780 mg, 20.0 eq., 12.0 mmol) and DMA (5 mL), sealed and allowed to stir at 130° C. for 16 h. EtOAc (50 mL) and sat. NaHCO3 (50 mL) are then added and the organic layer is washed with water (100 mL), brine (100 mL) and dried over Na2SO4. The crude solution is filtered, concentrated and purified by SiO2 flash chromatography using hexanes:Et2O (5:1) affording the title compound as a yellow oil. [mass expected (424.58); mass found (424.29)].

Workup

  1. customsealed
  2. washthe organic layer is washed with water (100 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationThe crude solution is filtered
  5. concentrationconcentrated
  6. custompurified by SiO2 flash chromatography

Sources & evidence

ORD record
ord-9b6390a6a7f446cd8b1e7fe8d3bc48ad
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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