Sodium borohydride → HCID 89579764, compound

HRID 928604Notes

Reaction equation

HRID 928604 reaction equation
N1C=CC=NC=1.CS([C:11]1[N:12]=[C:13]([N:26]2[CH2:31][CH2:30][CH:29]([CH2:32][O:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:28][CH2:27]2)[C:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][O:17][C:15]=2[N:16]=1)(=O)=O.[BH4-].[Na+]>C(O)C>[C:20]1([C:19]2[C:14]3[C:13]([N:26]4[CH2:31][CH2:30][CH:29]([CH2:32][O:33][CH2:34][CH2:35][N:36]5[CH2:37][CH2:38][CH2:39][CH2:40]5)[CH2:28][CH2:27]4)=[N:12][CH:11]=[N:16][C:15]=3[O:17][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 89579744HCID 89579744, compound

Product 1

HCID 89579764HCID 89579764, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methylsulphonyl-5-phenyl-4 [4-2-pyrrolidin-1-ylethoxymethyl-1-piperidyl]furo[2,3-d]-pyrimidine pyrimidine (75 mg, 0.15 mmol) in ethanol (5.0 mL) was treated with sodium borohydride (15 mg, 0.38 mmol) at 20° C. with continuous stirring for 30 min. A further 30 mg of sodium borohydride was added and the reaction was stirred at 20° C. for a further 1 h. A further 60 mg of sodium borohydride was added and the reaction was stirred at 20° C. for a further 1 hr then concentrated in vacuum to a gum and the residue partitioned between dichloromethane and water. The dichloromethane layer was separated, dried over sodium sulphate and concentrated in vacuum to a gum. The gum was purified by preparative HPLC to give 5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]furo[2,3-d]pyrimidine (53 mg, 0.13 mmol, 84%). 1H NMR (CDCl3) δ: 1.02 (2H, m), 1.5 (2H, m), 1.75 (6H, m), 2.45-2.8 (9H, m), 3.2 (2H, d, J=8 Hz), 3.5 (2H, t, J=8 Hz), 3.95 (2H, d, J=12 Hz), 7.35-7.45 (5H, m), 7.52 (1H, s), 8.45 (1H, s). LCMS RT=5.14 min. M+1=407.

Workup

  1. stirringthe reaction was stirred at 20° C. for a further 1 h
  2. stirringthe reaction was stirred at 20° C. for a further 1 hr
  3. concentrationthen concentrated in vacuum to a gum
  4. customthe residue partitioned between dichloromethane and water
  5. customThe dichloromethane layer was separated
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuum to a gum
  8. customThe gum was purified by preparative HPLC

Sources & evidence

ORD record
ord-28e0364f08d94727b6e22f4acead5019
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

Loading…