Lithium borohydride → Tert-butyl 4-(5-(2-(4-fluorophenyl)-1,3-dihydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 1498868Notes

Reaction equation

HRID 1498868 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([O-:29])=[O:28])[CH2:23][CH2:22]3)=[N:19][CH:20]=2)([CH2:13][OH:14])[C:9]([O:11]C)=O)=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:28])[CH2:23][CH2:22]3)=[N:19][CH:20]=2)([CH2:13][OH:14])[CH2:9][OH:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 1317342314-(5-(2-(4-Fluorophenyl)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 118023378Tert-butyl 4-(5-(2-(4-fluorophenyl)-1,3-dihydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylateYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-(2-(4-fluorophenyl)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate (700 mg, 1.5 mmol) in 20 mL of THF was cooled to −10° C., followed by the addition of LiBH4 (180 mg, 7.5 mmol) slowly. This mixture was allowed to warm to RT and stirred overnight. The reaction was quenched by MeOH (3 mL) and then concentrated in vacuo. The residue was purified by silica gel column (DCM:MeOH, 10:1) to obtain the desired product (300 mg, yield 47%) as a yellow foam. MS (ES+) C22H29FN4O4 requires: 432. found 433 [M+H]+; purity: 67% (UV254).

Workup

  1. customThe reaction was quenched by MeOH (3 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column (DCM:MeOH, 10:1)

Sources & evidence

ORD record
ord-6c52516ec68441a594c8e485c993410e
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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