Sodium triacetoxyborohydride → HCID 86648237, compound

HRID 1922819Notes

Reaction equation

HRID 1922819 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-2700b79e53044a0293272de5775f9334
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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