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Sodium triacetoxyborohydride → HCID 70832977, compound

HRID 1170526
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Reaction equation

HRID 1170526 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([CH:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[N:19]1([C:24]2[N:29]=[C:28]([C:30](=O)[CH3:31])[CH:27]=[C:26]([CH3:33])[N:25]=2)[CH:23]=[CH:22][N:21]=[CH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH:30]([C:28]3[CH:27]=[C:26]([CH3:33])[N:25]=[C:24]([N:19]4[CH:23]=[CH:22][N:21]=[CH:20]4)[N:29]=3)[CH3:31])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 534139731-(2-(1H-Imidazol-1-YL)-6-methylpyrimidin-4-YL)ethanoneHCID 58654344HCID 58654344, compound

Product 1

HCID 70832977HCID 70832977, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Pyrrolidine-2-carboxylic acid (benzo[1,3]dioxol-5-ylmethyl)-amide (85 mg, 0.34 mmol) was dissolved in dioxane (2.5 mL). Next, TsOH monohydrate (30 mg) and the 1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethanone (69 mg, 0.34 mmol) were added and the reaction mixture was microwaved for 20 mins at 130° C. Upon completion of heating, the solution was allowed to return to room temperature and the sodium triacetoxyborohydride (145 mg, 0.68 mmol) was added to the reaction vessel and it was allowed to stir at room temperature for an additional 16 hours. After this period, the solution was concentrated under vacuum, diluted in ethyl acetate (50 mL) and transferred to a separatory funnel. The organic layer was washed with 1M NaOH (50 mL), dried over Na2SO4 and concentrated down by vacuum to afford the crude product. This material was purified by Flash Chromatography (0-40% ACN/DCM gradient) to afford 12 mg (8%) of 1-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethyl]-pyrrolidine-2-carboxylic acid (benzo[1,3]dioxol-5-ylmethyl)-amide. Product isolated as a mixture of diasteromers; [M+H]+ 435.03.

Workup

  1. customthe reaction mixture was microwaved for 20 mins at 130° C
  2. temperatureUpon completion of heating
  3. customto return to room temperature
  4. waitAfter this period
  5. concentrationthe solution was concentrated under vacuum
  6. additiondiluted in ethyl acetate (50 mL)
  7. customtransferred to a separatory funnel
  8. washThe organic layer was washed with 1M NaOH (50 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated down by vacuum
  11. customto afford the crude product
  12. customThis material was purified by Flash Chromatography (0-40% ACN/DCM gradient)

Sources & evidence

ORD record
ord-4032852ef4c4458a8131d7fb89970256
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07825256B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes