Sodium triacetoxyborohydride → HCID 59605926, compound

HRID 1945645Notes

Reaction equation

HRID 1945645 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH:13]=O)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[CH:21]([C:24]1([OH:28])[CH2:27][NH:26][CH2:25]1)([CH3:23])[CH3:22].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][CH2:13][N:26]3[CH2:27][C:24]([CH:21]([CH3:23])[CH3:22])([OH:28])[CH2:25]3)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 221637913-(1-Methylethyl)-3-azetidinolHCID 59605819(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde

Product 1

HCID 59605926HCID 59605926, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (69 mg, 0.23 mmol) in DCE (5 mL) was added 3-isopropyl-azetidin-3-ol (27 mg, 0.23 mmol) and powdered 4 Å molecular sieves. The reaction mixture was stirred at room temperature for 2 h, sodium triacetoxyborohydride (99 mg, 0.47 mmol) was added and the resulting mixture stirred for a further 2 days. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-10% 2 M NH3/MeOH in DCM) to give the title compound as a pale yellow oil (30 mg, 33%). LCMS (Method H): RT=2.65 min, [M+H]+ 395.5

Workup

  1. stirringthe resulting mixture stirred for a further 2 days
  2. washwashed with MeOH
  3. washthe desired product eluted with 2 M NH3 in MeOH
  4. customThe resulting residue was purified by column chromatography (Si—PCC, 0-10% 2 M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-4bdd94fb28c846ef96953dfa85b1fd02
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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