Sodium borohydride → HCID 24745318, compound

HRID 552117Notes

Reaction equation

HRID 552117 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([C:19]4[CH:24]=[CH:23][N:22]=[C:21]([C:25](OCC)=[O:26])[CH:20]=4)[N:15]3[CH3:18])=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[N:15]3[CH3:18])=[CH:11][N:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58441989HCID 58441989, compound

Product 1

HCID 24745318HCID 24745318, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 30 mg (0.077 mmol, 1.0 eq.) of ethyl 4-(2-(4-fluorophenylamino)-9-methyl-9H-purin-8-yl)picolinate (I-15) in 3 mL of ethanol was added 58 mg (1.5 mmol, 20 eq.) of sodium borohydride. The mixture was stirred at room temperature for 16 h. The volatiles were removed in vacuo and the resulting residue was purified by semi-preparative HPLC to afford 0.9 mg (3%) of (4-(2-(4-fluorophenylamino)-9-methyl-9H-purin-8-yl)pyridine-2-yl)methanol (I-16).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-e3f9e92ba17b43759c7f18771a32f9a7
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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