Sodium borohydride → HCID 71239361, compound

HRID 1774617Notes

Reaction equation

HRID 1774617 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]3[CH2:25][CH2:24]3)=[C:18]([Cl:26])[CH:17]=2)[N:13]=[CH:12][N:11]=1)[C:3]([O:5][CH3:6])=[O:4].[BH4-].[Na+]>CO.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Cl:26][C:18]1[CH:17]=[C:16]([C:14]2[N:13]=[CH:12][N:11]=[C:10]([CH:9]3[NH:1][CH:2]([C:3]([O:5][CH3:6])=[O:4])[CH2:7][CH2:8]3)[CH:15]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH:23]1[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 117684692HCID 117684692, compound

Product 1

HCID 71239361HCID 71239361, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 887MethanolSolvent

Procedure

Silver triflate (0.17 g, 0.67 mmol) was added portion wise to a stirred solution of methyl (2S)-2-amino-5-[6-(3-chloro-4-cyclopropoxyphenyl)pyrimidin-4-yl]pent-4-ynoate (0.5 g, 1.3 mmol) in methanol (10 ml) and the mixture was stirred at room temperature overnight. After this time the solid precipitate was removed by filtration and the filtrate concentrated. The resulting residue was dissolved in methanol (5 ml), cooled to 0° C., treated with sodium borohydride (0.2 g, 5.0 mmol) and stirred at 0° C. for 2 hours. After this time the reaction mixture was quenched by the careful addition of saturated sodium bicarbonate (1 ml), the mixture was concentrated and the resulting residue partitioned between ethyl acetate (20 ml) and water (10 ml). The organic layer was removed, dried (MgSO4), filtered and concentrated. The residue was purified by prep HPLC to give the title compound (0.03 g, 5% yield) as a brown oil. Tr=2.22 min m/z (ES+) (M+H+) 373.

Workup

  1. customAfter this time the solid precipitate was removed by filtration
  2. concentrationthe filtrate concentrated
  3. dissolutionThe resulting residue was dissolved in methanol (5 ml)
  4. temperaturecooled to 0° C.
  5. stirringstirred at 0° C. for 2 hours
  6. customAfter this time the reaction mixture was quenched by the careful addition of saturated sodium bicarbonate (1 ml)
  7. concentrationthe mixture was concentrated
  8. customthe resulting residue partitioned between ethyl acetate (20 ml) and water (10 ml)
  9. customThe organic layer was removed
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-cf83621044614dafab871474f9d3edaf
Source dataset
uspto-grants-2016_02
Patent number
US09260422B2

Reaction notes

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