Sodium triacetoxyborohydride → HCID 86648237, compound

HRID 1945652Notes

Reaction equation

HRID 1945652 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:12]=O)[N:8]2[CH3:11])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.[C@H:20]12[CH2:26][C@H:23]([NH:24][CH2:25]1)[CH2:22][N:21]2[C:27]([CH3:31])([CH3:30])[CH2:28][OH:29].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][N:24]3[CH2:25][C@@H:20]4[CH2:26][C@H:23]3[CH2:22][N:21]4[C:27]([CH3:31])([CH3:30])[CH2:28][OH:29])[N:8]2[CH3:11])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 596034722-Chloro-9-methyl-6-morpholino-9H-purine-8-carbaldehydeHCID 67492507HCID 67492507, compound

Product 1

HCID 86648237HCID 86648237, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-chloro-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (235 mg, 0.83 mmol), (2-(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-yl-2-methylpropan-1-ol (168 mg, 0.99 mmol) and molecular sieves (4 Å, powdered, 1 g) in DCE (10 mL) was stirred at ambient temperature for 4 h. Sodium triacetoxyborohydride (265 mg, 1.25 mmol) was added and the mixture stirred for 18 h, then loaded onto an Isolute® SCX-2 cartridge (25 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; 90:10) to afford the title compound as a tan solid (50 mg, 14%). LCMS (Method H): RT=2.39 min, M+H+=436.

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; 90:10)

Sources & evidence

ORD record
ord-6d9e4bee7ea74a70b1949e324d1251eb
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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