Potassium Carbonate → (5-But-3-ynylpyridin-2-yl)isopropylamine

HRID 734903Notes

Reaction equation

HRID 734903 reaction equation
[N+](=[C:3](P(=O)(OC)OC)C(=O)C)=[N-].[CH:13]([NH:16][C:17]1[N:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]=O)=[CH:19][CH:18]=1)([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO.O.CCOC(C)=O>[CH2:23]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][CH:13]([CH3:15])[CH3:14])=[N:22][CH:21]=1)[CH2:24][C:25]#[CH:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 860769953-(6-Isopropylaminopyridin-3-yl)propionaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86076998(5-But-3-ynylpyridin-2-yl)isopropylamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere 361 mg (1.88 mmol) of dimethyl (1-diazo-2-oxopropyl)phosphonate in 4 mL of MeOH was added to a solution of 300 mg (1.57 mmol) of 3-(6-isopropylaminopyridin-3-yl)propionaldehyde and 434 mg (3.14 mmol) of potassium carbonate in 6 mL of MeOH and the mixture was stirred for 3 hours at RT. The reaction mixture was diluted with water and EtOAc, combined with saturated aqueous sodium hydrogen carbonate solution, and the organic phase was separated off, extracted with water, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Yield: 220 mg (75% of theoretical); C12H16N2 (M=188.269); calc.: molpeak (M+H)+:189; found: molpeak (M+H)+:189; HPLC-MS: 4.09 minutes (method G).

Workup

  1. customthe organic phase was separated off
  2. extractionextracted with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. custom4.09 minutes (method G)

Sources & evidence

ORD record
ord-d9ca9593b57d40b0841ab88b537a8b9b
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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