Sodium borohydride → HCID 57639375, compound

HRID 2111572Notes

Reaction equation

HRID 2111572 reaction equation
[OH:1][C:2]1([C:31](OC)=[O:32])[CH2:7][CH2:6][CH:5]([N:8]2[C:16]([NH:17][C:18]3[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=3[F:26])=[N:15][C:14]3[C:9]2=[N:10][C:11]([NH:27][CH:28]([CH3:30])[CH3:29])=[N:12][CH:13]=3)[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:32][CH2:31][C:2]1([OH:1])[CH2:3][CH2:4][CH:5]([N:8]2[C:16]([NH:17][C:18]3[C:19]([F:26])=[CH:20][C:21]([F:25])=[CH:22][C:23]=3[F:24])=[N:15][C:14]3[C:9]2=[N:10][C:11]([NH:27][CH:28]([CH3:29])[CH3:30])=[N:12][CH:13]=3)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66672661HCID 66672661, compound

Product 1

HCID 57639375HCID 57639375, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-hydroxy-4-{2-[(methylethyl)amino]-8-[(2,4,6-trifluorophenyl)amino]purin-9-yl}cyclohexanecarboxylate (0.300 g, 0.6 mmol) was dissolved in 3 mL of dry methanol. The solution was cooled to 0° C. before addition of solid sodium borohydride (0.300 g, 7.92 mmol). After 1 h at low temperature, the reaction was warmed to rt and stirred overnight. The reaction was quenched with 5 mL of a saturated solution of ammonium chloride. The crude product was extracted with dichloromethane (four times). The product was purified by column chromatography (75% ethyl acetate in hexanes) followed by semi-preparative HPLC. The fractions were neutralized using a resin-exchange column. (0.101 g, 37% yield). M+1: 451.

Workup

  1. customThe reaction was quenched with 5 mL of a saturated solution of ammonium chloride
  2. extractionThe crude product was extracted with dichloromethane (four times)
  3. customThe product was purified by column chromatography (75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8a6489fe446641cc82999cd454fd5e5f
Source dataset
uspto-grants-2009_04
Patent number
US07521446B2

Reaction notes

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