1,2-Dichloroethane → HCID 59605782, compound

HRID 1923060Notes

Reaction equation

HRID 1923060 reaction equation
[CH3:1][N:2]1[C:10]([CH:11]=O)=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[NH:19]1[CH2:22][CH:21]([CH:23]([OH:27])[CH:24]([CH3:26])[CH3:25])[CH2:20]1.C(O[BH-](O[C:38](=O)[CH3:39])OC(=O)C)(=O)C.[Na+].Cl[CH2:43][CH2:44]Cl>>[CH2:8]([C:3]1[N:2]([C:5]2[N:4]=[C:3]3[C:8]([N:9]=[C:10]([CH2:11][N:19]4[CH2:22][CH:21]([CH:23]([OH:27])[CH:24]([CH3:26])[CH3:25])[CH2:20]4)[N:2]3[CH3:1])=[C:7]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:6]=2)[C:10]2[CH:11]=[CH:43][CH:44]=[CH:39][C:38]=2[N:4]=1)[CH3:7]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59606118HCID 59606118, compoundHCID 86648253HCID 86648253, compound

Product 1

HCID 59605782HCID 59605782, compoundYield 37%

Procedure

A mixture of 242-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (125 mg, 0.32 mmol), 1-azetidin-3-yl-2-methylpropan-1-ol (50 mg, 0.38 mmol) and 4 Å molecular sieves (1.0 g) in 1,2-dichloroethane (5 mL) was stirred at RT under nitrogen atmosphere for 5 h. Sodium triacetoxyborohydride (102 mg, 0.48 mmol) was added and the resulting reaction mixture was stirred at RT for 16 h. The solvent was reduced in vacuo and the residue was loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with DCM/MeOH, the desired product was subsequently eluted using a mixture of 2M NH3 in MeOH and DCM. The solvents were reduced in vacuo to afford 313 as an off-white foam (60 mg, 37%). LCMS (Method G): RT 6.95 min, [M+H]+ 505. 1H NMR (400 MHz, CDCl3): δ 7.99-7.95 (1 H, m), 7.72-7.71 (1 H, m), 7.23 (2 H, m), 4.32 (4 H, br s), 3.85-3.78 (9 H, m), 3.47-3.45 (3 H, m), 3.32 (2 H, q, J=7.48 Hz), 3.25 (1 H, t, J=6.66 Hz), 3.13 (1 H, t, J=6.66 Hz), 2.66-2.65 (1 H, m), 1.62-1.60 (2 H, m), 1.41 (3 H, t, J=7.48 Hz), 0.87(6 H, dd, J=11.85, 6.78 Hz)

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at RT for 16 h
  3. washThe cartridge was washed with DCM/MeOH
  4. washthe desired product was subsequently eluted
  5. additiona mixture of 2M NH3 in MeOH and DCM

Sources & evidence

ORD record
ord-04c6380e765843189763b385494aee40
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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