Sodium triacetoxyborohydride → HCID 59605925, compound

HRID 1945906Notes

Reaction equation

HRID 1945906 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.[NH:29]1[CH2:32][CH:31]([C:33]([N:35]2[CH2:38][CH2:37][CH2:36]2)=[O:34])[CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[N:35]1([C:33]([CH:31]2[CH2:32][N:29]([CH2:11][C:10]3[N:2]([CH3:1])[C:3]4[C:8]([N:9]=3)=[C:7]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:6]=[C:5]([N:19]3[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=[C:20]3[CH3:28])[N:4]=4)[CH2:30]2)=[O:34])[CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 596054202-(2-methylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehydeHCID 59605486HCID 59605486, compound

Product 1

HCID 59605925HCID 59605925, compoundYield 23%

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 (100 mg, 0.27 mmol) and azetidin-3-ylazetidin-1-ylmethanone (45 mg, 0.31 mmol) in DCE (3 mL) was stirred at ambient temperature for 90 min. Sodium triacetoxyborohydride (86 mg, 0.41 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, EtOAc:MeOH; 100:0 to 90:10 to 85:15) to afford 347 as a white solid (30 mg, 23%). LCMS (Method G): RT=5.33 min, M+H+=502. 1H NMR (CDCl3, 400 MHz) δ 8.07 (m, 1 H); 7.69 (m, 1 H); 7.28 (m, 2 H); 4.35 (m, 4 H); 4.13-4.00 (m, 4 H); 3.87 (m, 6 H); 3.82 (s, 3 H); 3.68-3.58 (m, 2 H); 3.53-3.45 (m, 2 H); 3.34-3.26 (m, 1 H); 2.96 (s, 3 H) and 2.33-2.23 (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, EtOAc:MeOH; 100:0 to 90:10 to 85:15)

Sources & evidence

ORD record
ord-7dd31f4b214e4d3591fe57ec4c4191a9
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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