Sodium borohydride → 5-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-morpholin-4-yl-pyrimidin-4-ylamide

HRID 356653Notes

Reaction equation

HRID 356653 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:3]=1[O:4][C:5]1[C:6]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][N:24]=2)(=[O:22])=[O:21])=[N:7][C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:9][C:10]=1[CH:11]=[O:12].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:3]=1[O:4][C:5]1[C:6]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][N:24]=2)(=[O:22])=[O:21])=[N:7][C:8]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[N:9][C:10]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 223778605-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-morpholin-4-yl-pyrimidin-4-ylamide

Product 1

HCID 178683755-Isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-morpholin-4-yl-pyrimidin-4-ylamideYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

0.1 g of the compound obtained in Example 37 in 3 ml of ethanol was treated with 0.014 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 1 N HCl. The organic phase was washed with water and dried, the solvent was evaporated and the residue was chromatographed over silica gel with chloroform-methanol. After recrystallization from dichloromethane-ethanol there was obtained 0.072 g of 5-isopropyl-pyridine-2-sulphonic acid 5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-morpholin-4-yl-pyrimidin-4-ylamide. M.p. 105° C.

Workup

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

Sources & evidence

ORD record
ord-90108591dc844b59ab952ed3de73580d
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

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