Sodium triacetoxyborohydride → HCID 59605696, compound

HRID 1946089Notes

Reaction equation

HRID 1946089 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]=O)[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2].[C:30]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][C:35]1=[O:40])([CH3:33])([CH3:32])[CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:30]([N:34]1[CH2:39][CH2:38][N:37]([CH2:18][C:13]2[N:14]([CH3:17])[C:15]3[C:11]([N:12]=2)=[C:10]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[N:9]=[C:8]([N:7]2[C:6]4[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=4[N:4]=[C:3]2[CH2:1][CH3:2])[N:16]=3)[CH2:36][C:35]1=[O:40])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 230810841-tert-Butyl-2-piperazinoneHCID 596059872-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

Product 1

HCID 59605696HCID 59605696, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.15 g, 0.39 mmol), 1-tert-butylpiperazin-2-one (0.072 g, 0.46 mmol) and 4 Å molecular sieves (0.4 g) in DCE (5 mL) was stirred for 4 h at room temperature. Sodium triacetoxyborohydride (0.163 g, 0.77 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95) to give 577 as a white solid (0.178 g, 87%). LCMS (Method I): RT=3.59 min, [M+H]+ 532.2 1H NMR (400 MHz, DMSO-d6): δ 8.03-7.98 (m, 1 H), 7.65-7.60 (m, 1 H), 7.26-7.21 (m, 2 H), 4.50-3.95 (m, 5 H), 3.83-3.79 (m, 6 H), 3.78 (m, 4 H), 3.27 (q, J=7.4 Hz, 2 H), 3.08 (s, 2 H), 2.69-2.64 (m, 2 H), 1.36 (s, 9 H), 1.34 (t, J=7.4 Hz, 3 H)

Workup

  1. stirringthe reaction mixture was stirred for 18 h at room temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95)

Sources & evidence

ORD record
ord-b588dd4510f545b4b71737e1639ebaa8
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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