Sodium borohydride → HCID 131727373, compound

HRID 2240134Notes

Reaction equation

HRID 2240134 reaction equation
[S:1]([O:8][C:9]1[C:13]2[N:14]=[C:15]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[N:16]=[C:17]([NH:18][CH2:19][CH2:20][CH3:21])[C:12]=2[S:11][CH:10]=1)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[BH4-].[Na+]>CO>[S:1]([O:8][CH:9]1[C:13]2[N:14]=[C:15]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=4)[CH2:24][CH2:23]3)[N:16]=[C:17]([NH:18][CH2:19][CH2:20][CH3:21])[C:12]=2[S:11][CH2:10]1)([C:4]([F:6])([F:5])[F:7])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131727374HCID 131727374, compound

Product 1

HCID 131727373HCID 131727373, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.050 g (0.12 mmol) of 2-[4-(4-chlorophenyl)piperazin-1-yl]-4-propylaminothieno[3,2-d]pyrimidin-7-ol triflate (IX) is dissolved in 1 mL of methanol and 0.020 g (0.53 mmol) of sodium borohydride is added. The reaction mixture is stirred for 16 hours at ambient temperature, then concentrated by evaporation. The residue is purified by chromatography using HPLC through an RP column (column: Microsorb, RP-C18). Corresponding fractions are combined and lyophilized. 0.013 g of product X (20%) is obtained as a powder. 1H NMR (400 MHz, DMSO): 7.26 (2H, d); 7.00 (2H, d); 5.15-5.09 (1H, m); 3.86-3.79 (4H, m), 3.63-3.55 (2H, m); 3.42-3.33 (2H, m); 3.28-3.22 (4H, m); 3.18-3.11 (1H, m); 1.63-1.52 (2H, m); 0.88 (3H, t).

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-48c267b1a0434ab4a8eddcf726313e92
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

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