Sodium triacetoxyborohydride → HCID 86648238, compound

HRID 1922820Notes

Reaction equation

HRID 1922820 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.[CH3:20][S:21]([N:24]1[CH2:29][C@@H:28]2[CH2:30][C@H:25]1[CH2:26][NH:27]2)(=[O:23])=[O: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][N:27]3[CH2:26][C@@H:25]4[CH2:30][C@H:28]3[CH2:29][N:24]4[S:21]([CH3:20])(=[O:23])=[O:22])[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 67492462HCID 67492462, compound

Product 1

HCID 86648238HCID 86648238, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-chloro-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (227 mg, 0.81 mmol), (1S,4S)-2-methanesulfonyl-2,5-diazabicyclo[2.2.1]heptane (170 mg, 0.97 mmol) and molecular sieves (4 Å, powdered, 1 g) in DCE (12 mL) was stirred at ambient temperature for 3 h. Sodium triacetoxyborohydride (255 mg, 1.20 mmol) was added and the mixture stirred for 17 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; 98:2) to afford the title compound as a white solid (350 mg, 98%). LCMS (Method H): RT=2.51 min, M+H+=442.

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; 98:2)

Sources & evidence

ORD record
ord-186929f308ee4d018c12ebbc7be7596a
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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