Ethanol → 4-tert-butyl-N-[3-(2-{[2-(hydroxymethyl)-5-pyrimidinyl]oxy}ethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1368627Notes

Reaction equation

HRID 1368627 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24]C3N=CC(C=O)=CN=3)[C:16]=2[C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+:43].[CH2:44]([OH:46])[CH3:45]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:16]3[CH:17]=[N:43][C:45]([CH2:44][OH:46])=[N:14][CH:15]=3)[C:16]=2[C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 222819404-(tert-butyl)-N-[3-{2-[(5-formyl-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Product 1

HCID 98076364-tert-butyl-N-[3-(2-{[2-(hydroxymethyl)-5-pyrimidinyl]oxy}ethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Procedure

To 4-(tert-butyl)-N-[3-{2-[(5-formyl-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Example 38) (25 mg) in ethanol (0.5 ml) at room temperature was added sodium borohydride (2 mg) the mixture was stirred for 1 hr. The reaction was treated with ammonium chloride (aq. sat. 5 ml) and extracted with diethyl ether (1×5 ml, 1×2 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title compound as a white solid (20 mg).

Workup

  1. extractionextracted with diethyl ether (1×5 ml, 1×2 ml)
  2. dry with materialThe organic fraction was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48c2b2a1bd5a4c20b035d41bdd02e0f2
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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