Sodium borohydride → HCID 131733643, compound

HRID 1752448Notes

Reaction equation

HRID 1752448 reaction equation
NC(=O)[C@@H](N[C:6]1[CH:11]=[C:10]([C:12](=[O:14])[NH2:13])[N:9]=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[C:19]([CH:24]=2)[C:20](OC)=[O:21])[N:7]=1)C.[BH4-].[Na+]>C(O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][C:18]2[CH:17]=[CH:16][C:15]([C:8]3[N:9]=[C:10]([C:12]([NH2:13])=[O:14])[CH:11]=[CH:6][N:7]=3)=[CH:24][C:19]=2[CH2:20][OH:21])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71283454HCID 71283454, compound

Product 1

HCID 131733643HCID 131733643, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-methyl 5-(4-((1-amino-1-oxopropan-2-yl)amino)-6-carbamoylpyrimidin-2-yl)-2-(4-fluorophenoxy)benzoate (50 mg, 0.11 mmol) in ethyl alcohol (1 mL) at room temperature was added NaBH4 (21 mg, 0.55 mmol). The mixture was stirred at room temperature for 2 h and quenched with addition of MeOH. The mixture was poured onto silica gel and purified via chromatography with 0 to 20% MeOH in CH2CH2 to provide (S)-6-(1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-fluorophenoxy)-3-(hydroxymethyl)phenyl)pyrimidine-4-carboxamide (30 mg, 0.07 mmol) as white solid. 1H NMR (400 MHz, DMSO-d6): 8.57 (1H, d, J=2 Hz), 8.27 (1H, dd, J=2.4, 8.8 Hz), 7.05-6.94 (5H, m), 6.70 (1H, d, J=8.4 Hz), 4.68 (2H, s), 4.50 (1H, s), 1.42 (3H, d, J=7.2 Hz). LC/MS: m/z=426 [M+H]+.

Workup

  1. customquenched with addition of MeOH
  2. additionThe mixture was poured onto silica gel
  3. custompurified via chromatography with 0 to 20% MeOH in CH2CH2

Sources & evidence

ORD record
ord-c748db47b3b44ee89f9b98e52eada5a5
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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