Lithium borohydride → HCID 118023536, compound

HRID 1498865Notes

Reaction equation

HRID 1498865 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:18][CH:19]=2)([CH3:13])[C:9](OC)=[O:10])=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:18][CH:19]=2)([CH3:13])[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 118023247HCID 118023247, compound

Product 1

HCID 118023536HCID 118023536, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 4-(5-(2-(4-fluorophenyl)-1-methoxy-1-oxopropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate (0.4 g, 0.9 mmol) in THF (10 mL) was added LiBH4 (40 mg, 1.8 mmol). After stirred at RT for 2 h, the reaction was quenched by aq. NH4Cl and extracted with EA. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was passed a column (silica gel, PE:EA=1:1) to afford the title compound (225 mg, 60%) as a yellow solid. MS (ES+) C22H29FN4O3 requires: 416. found: 417 [M+H]+.

Workup

  1. customthe reaction was quenched by aq. NH4Cl
  2. extractionextracted with EA
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89360e370ee44d5682bb48f7c54e44a4
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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