Lithium borohydride → HCID 178504232, compound

HRID 1172441Notes

Reaction equation

HRID 1172441 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:13]=[CH:12][N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:10]=2)[N:5]=[C:4]([C:22](OC)=[O:23])[CH:3]=1.[BH4-].[Li+]>O1CCCC1.CO>[OH:23][CH2:22][C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[C:6]([NH:8][C:9]2[CH:13]=[CH:12][N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:10]=2)[N:5]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 178498562HCID 178498562, compound

Product 1

HCID 178504232HCID 178504232, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To 16 g of methyl 4-hydroxy-6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyridine-2-carboxylate dissolved in 200 ml of tetrahydrofuran, 2.0 M of lithium borohydride dissolved in 30 ml of tetrahydrofuran solution was added, and the mixture was stirred at 60° C. for 1 hour. The resulting mixture was cooled to 0° C., and then 10% hydrochrolic acid in methanol was added thereto to adjust the pH of the solution to 4. After stirred 30 minutes at room temperature, the mixture was concentrated to give the title compound.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was cooled to 0° C.
  3. stirringAfter stirred 30 minutes at room temperature
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-df19d252b42e4cccafb536f4aad26372
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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