Sodium triacetoxyborohydride → 4-[2-(2-Chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]-1-isopropylpiperazin-2-one

HRID 1945646Notes

Reaction equation

HRID 1945646 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH:13]=O)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[CH:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][C:25]1=[O:30])([CH3:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH2:13][N:27]3[CH2:28][CH2:29][N:24]([CH:21]([CH3:23])[CH3:22])[C:25](=[O:30])[CH2:26]3)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150574011-(Propan-2-yl)piperazin-2-oneHCID 59605819(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde

Product 1

HCID 596059634-[2-(2-Chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]-1-isopropylpiperazin-2-oneYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (167 mg, 0.57 mmol) in DCE (10 mL) was added 1-isopropylpiperazin-2-one (87 mg, 0.61 mmol) and powdered 4 Å molecular sieves. The reaction mixture was stirred at room temperature for 1 h, sodium triacetoxyborohydride (239 mg, 1.13 mmol) was added and the resulting mixture stirred for a further 16 h. The reaction mixture was filtered through Celite®, loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-10% 2 M NH3/MeOH in DCM) to give the title compound as a pale yellow oil (51 mg, 33%). LCMS (Method H): RT=3.31 min, [M+H]+ 422.5

Workup

  1. stirringthe resulting mixture stirred for a further 16 h
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washwashed with MeOH
  4. washthe desired product eluted with 2 M NH3 in MeOH
  5. customThe resulting residue was purified by column chromatography (Si—PCC, 0-10% 2 M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-2644ebbd068b47359ff4741f3923bb73
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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