Potassium tert-butoxide → HCID 86677571, compound

HRID 2401114Notes

Reaction equation

HRID 2401114 reaction equation
CO[C:3](=[O:21])[C:4]([CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[N:16][C:17]([Cl:20])=[N:18][CH:19]=1)([CH2:9][CH3:10])[CH2:5][CH2:6][O:7]C.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[Cl:20][C:17]1[N:16]=[CH:15][C:14]([N:13]2[CH2:12][CH2:11][C:4]3([CH2:9][CH2:10][O:7][CH2:6][CH2:5]3)[C:3]2=[O:21])=[CH:19][N:18]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxide3×HCID 86677570HCID 86677570, compound

Product 1

HCID 86677571HCID 86677571, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[2-(2-chloro-pyrimidin-5-ylamino)-ethyl]-2-ethyl-4-methoxy-butyric acid methyl ester (0.083 g, 0.277 mmol) in THF (6 mL) was added a solution of potassium t-butoxide (1 M in THF) (0.5 mL), and the solution was allowed to stir at room temperature for 1 hour. An additional 0.5 mL of potassium t-butoxide (1 M in THF) was added and stirred for 2 hours. The reaction was still not complete, thus 0.75 mL of potassium t-butoxide (1 M in THF) was added and stirred for 4 hours. The reaction mixture was then diluted with ethyl acetate (20 mL), quenched with water (3 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were washed with brine, and concentrated under vacuum to afford 0.07 (95%) of title compound.

Workup

  1. stirringstirred for 2 hours
  2. stirringstirred for 4 hours
  3. customquenched with water (3 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with brine
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-752ea8cae2094f3d911df34d8f47c581
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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