Sodium borohydride → 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

HRID 37094

Reaction equation

HRID 37094 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH:31]=[O:32])[N:18]=[C:17]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH2:31][OH:32])[N:18]=[C:17]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:16]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 199347764-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

Product 1

HCID 199347574-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamideYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide in 300 mi of ethanol were treated with 0.9 g of sodium borohydride. The reaction mixture was stirred at 80° C. for 1 hour. Thereafter, the ethanol was distilled off and the residue was partitioned between chloroform and 1N HCI. The organic phase was washed with water and dried, the solvent was evaporated and the residue was chromatographed over silica gel with dichloromethane. After recrystallization from dichloromethane-ethanol there were obtained 4.6 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide, m.p. 103° C., MS: M=563.

Workup

  1. distillationThereafter, the ethanol was distilled off
  2. customthe residue was partitioned between chloroform and 1N HCI
  3. washThe organic phase was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customthe residue was chromatographed over silica gel with dichloromethane
  7. customAfter recrystallization from dichloromethane-ethanol there

Sources & evidence

ORD record
ord-051fa8df7835470fb60cb7bf7478776f
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Linked notes

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