Lithium borohydride → HCID 178418978, compound

HRID 480636Notes

Reaction equation

HRID 480636 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:14][CH:13]=2)[N:8]=[C:7]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[CH:6]=1)=O.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][C:5]1[N:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:16][CH:17]=2)[N:8]=[C:7]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 178418985HCID 178418985, compound

Product 1

HCID 178418978HCID 178418978, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [6-methoxycarbonyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (2 g, 4.85 mmol) in THF (100 mL) is added lithium borohydride (0.32 g, 14.5 mmol). The reaction mixture is stirred at 50° C. for 1.5 hours. The reaction is then quenched with dilute HCl and extracted with ethyl acetate. The organic layer is successively washed with aqueous saturated NaHCO3 and brine, dried over MgSO4 and evaporated. The solid residue is triturated in ethyl acetate and the resulting white solid is collected by filtration to give the desired product [6-hydroxymethyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. customThe reaction is then quenched with dilute HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is successively washed with aqueous saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe solid residue is triturated in ethyl acetate
  7. filtrationthe resulting white solid is collected by filtration

Sources & evidence

ORD record
ord-bfdedcf78251420d973bcf09886af12b
Source dataset
uspto-grants-2003_11
Patent number
US06653301B2

Reaction notes

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