Sodium borohydride → 1-(3-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-3-(tritylamino)-1H-pyrazole-4-carbonitrile

HRID 1025650Notes

Reaction equation

HRID 1025650 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH:49]=[O:50])=[C:18]([N:22]3[CH:26]=[C:25]([C:27]#[N:28])[C:24]([NH:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(Cl)Cl.CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:49][OH:50])=[C:18]([N:22]3[CH:26]=[C:25]([C:27]#[N:28])[C:24]([NH:29][C:30]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[N:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866737261-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-(trityl-amino)-1H-pyrazole-4-carbonitril

Product 1

HCID 710084231-(3-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-3-(tritylamino)-1H-pyrazole-4-carbonitrileYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-(trityl-amino)-1H-pyrazole-4-carbonitril (632 mg, 0.965 mmol) in methylene chloride (20 mL) and methanol (10 mL), at 0° C. was added sodium borohydride (37 mg, 0.965 mmol). The resulting turbid reaction mixture was stirred at 0° C. for 5 minutes and then allowed to stir at room temperature for 10 minutes. The reaction was then judged to be complete by TLC. The volatiles removed in vacuo and the crude product was bound to silica gel and purified over a 40 g silica gel cartridge eluting the column with a 20-50% EtOAc/hexanes gradient to give 1-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-(trityl-amino)-1H-pyrazole-4-carbonitrile (482 mg, 76%).

Workup

  1. customThe resulting turbid reaction mixture
  2. stirringto stir at room temperature for 10 minutes
  3. customThe volatiles removed in vacuo
  4. custompurified over a 40 g silica gel cartridge
  5. washeluting the column with a 20-50% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-d3a42d0dae894ee49b35f3e67e9d390e
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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