Sodium triacetoxyborohydride → HCID 59605752, compound

HRID 1922803Notes

Reaction equation

HRID 1922803 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.Cl.[O:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:30][NH:29][CH2:28]2)[CH2:23][CH2:22]1.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:29]3[CH2:30][CH:27]([CH:24]4[CH2:25][CH2:26][O:21][CH2:22][CH2:23]4)[CH2:28]3)[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 177856433-(oxan-4-yl)azetidine hydrochlorideHCID 596034722-Chloro-9-methyl-6-morpholino-9H-purine-8-carbaldehyde

Product 1

HCID 59605752HCID 59605752, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 2-chloro-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.173 g, 0.65 mmol), 3-(tetrahydropyran-4-yl)azetidine hydrochloride (0.138 g, 0.78 mmol) and 4 Å molecular sieves (0.9 g) in DCE (7 mL). The reaction mixture was stirred for 5 h at room temperature. Sodium triacetoxyborohydride (0.274 g, 1.29 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The suspension was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MeOH:EtOAc, gradient 0:100 to 10:90) to give 2-Chloro-9-methyl-6-morpholin-4-yl-8-[3-(tetrahydropyran-4-yl)azetidin-1-ylmethyl]-9H-purine as a white foam (0.117 g, 45%). LCMS (Method A): RT=2.40 min, [M+H]+ 407.2

Workup

  1. stirringthe reaction mixture was stirred for 18 h at room temperature
  2. filtrationThe suspension was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (Si—PPC, MeOH:EtOAc, gradient 0:100 to 10:90)

Sources & evidence

ORD record
ord-5c9f9079cf1440378f6218c8ff8c7318
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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