Sodium Bicarbonate → HCID 178520971, compound

HRID 1020163Notes

Reaction equation

HRID 1020163 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]2[N:23]=[CH:22][C:21]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][N:19]=2)[CH2:13][CH2:12]1)=O.C([O-])(O)=O.[Na+]>C1COCC1.[Cl-].[Na+].O>[C:26]1([C:25]#[C:24][C:21]2[CH:20]=[N:19][C:18]([NH:17][C@H:14]3[CH2:15][CH2:16][C@H:11]([CH2:9][OH:8])[CH2:12][CH2:13]3)=[N:23][CH:22]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 178501205HCID 178501205, compound

Product 1

HCID 178520971HCID 178520971, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suspension of LiAlH4 (17 mg, 0.44 mmol) in 10 ml THF was added at 0-5° C. within 15 min a solution of trans-4-(5-phenylethynyl-pyrimidin-2-ylamino)-cyclohexanecarboxylic acid methyl ester (40 mg, 0.12 mmol) in 5 ml of THF. The reaction mixture was stirred for 30 min at 0-5° C. Saturated NaHCO3 solution and brine were added to the reaction mixture which was extracted three times with dichloromethane. The combined organic phases were washed with brine, dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 2:1). The desired compound was obtained as a light yellow solid (29 mg, 81%), MS: m/e=308.5 (M+H+).

Workup

  1. extractionwas extracted three times with dichloromethane
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-d26e081b65a14cc990926a43336be67e
Source dataset
uspto-grants-2014_05
Patent number
US08716316B2

Reaction notes

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