Sodium triacetoxyborohydride → HCID 67492692, compound

HRID 1945916Notes

Reaction equation

HRID 1945916 reaction equation
[CH3:1][N:2]1[C:10]([CH:11]=O)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]1[CH3:28])=[N:6][C:7]=2[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[N:29]1([C:34]([CH:36]2[CH2:40][CH2:39][NH:38][CH2:37]2)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][N:2]1[C:10]([CH2:11][N:38]2[CH2:39][CH2:40][CH:36]([C:34]([N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)=[O:35])[CH2:37]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]1[CH3:28])=[N:6][C:7]=2[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 57387562HCID 57387562, compoundHCID 596054202-(2-methylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

Product 1

HCID 67492692HCID 67492692, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 9-methyl-2-(2-methylbenzoimidazol-1-yl)-6-morpholin-4-yl-9H-purine-8-carbaldehyde (105 mg, 0.28 mmol) and pyrrolidin-1-yl-1-pyrrolidin-3-ylmethanone (60 mg, 0.36 mmol) in DCE (6 mL) was stirred at ambient temperature for 2 h. Sodium triacetoxyborohydride (96 mg, 0.45 mmol) was added and the mixture stirred for 18 h, then loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2 M NH3 in MeOH. The product was collected and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; gradient from 100:0 to 70:30) to afford 364 as a white solid (110 mg, 74%). LCMS (Method G): RT=6.10 min, M+H+=530. 1H NMR (CDCl3, 400 MHz) δ 8.08 (m, 1 H); 7.70 (m, 1 H); 7.27 (m, 2 H); 4.35 (m, 4 H); 3.93 (s, 2 H); 3.92-3.81 (m, 7 H); 3.50-3.38 (m, 4 H); 3.19-3.08 (m, 1 H); 2.99 (m, 1 H); 2.94 (s, 3 H); 2.86 (m, 2 H); 2.70 (m, 1 H); 2.12 (m, 2 H); 2.02-1.90 (m, 2 H) and 1.91-1.81 (m, 2 H)

Workup

  1. washThe cartridge was then washed with methanol
  2. washthe desired product was subsequently eluted
  3. customThe product was collected
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; gradient from 100:0 to 70:30)

Sources & evidence

ORD record
ord-cb8f0eb49c634fc483c319d2c1fb0c18
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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