Sodium borohydride → HCID 9922188, compound

HRID 431255Notes

Reaction equation

HRID 431255 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:13]=2)[CH:5]=1.COC(=O)C1C=CC=C(/C=C/C2N=C(Cl)C=C(C)N=2)C=1.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>CO.C1COCC1>[CH3:18][C:16]1[CH:15]=[C:14]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[N:13]=[C:12](/[CH:11]=[CH:10]/[C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][CH:7]=2)[N:17]=1

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 69565711HCID 69565711, compoundHCID 86585401HCID 86585401, compound

Product 1

HCID 9922188HCID 9922188, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 60 mg of (E)-3-[2-(4-methyl-6-pyrrolidin-1-yl-pyrimidin-2-yl)-vinyl]-benzoic acid methyl ester, product of example 40, in MeOH/THF (each 2 ml) was treated at RT with 41 mg (0.37 mmol) CaCl2 followed by 28 mg (0.74 mmol) NaBH4 and then stirred for 18 h at RT until completion of the reaction according to TLC analysis. The reaction mixture was partitioned between diluted aqueous HCl and EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was applied to a short silica gel column with CH2Cl2/MeOH (95/%) as eluent. Combination of the purified fractions and concentration in vacuo gave 10 mg (18%) of the desired (E){3-[2-(4-methyl-6-pyrrolidin-1-yl-pyrimidin-2-yl)-vinyl]-phenyl}-methanol as a white solid. ISP mass spectrum, m/e: 296.4 (M+1 calculated for C18H21ClN3O: 296).

Workup

  1. customThe reaction mixture was partitioned between diluted aqueous HCl and EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-468defb7e0394645b9121afc98d1955d
Source dataset
uspto-grants-2003_12
Patent number
US06657060B2

Reaction notes

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