Sodium triacetoxyborohydride → HCID 59605905, compound

HRID 1923126Notes

Reaction equation

HRID 1923126 reaction equation
[CH3:1][N:2]1[C:10]([CH:11]=O)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]1[CH3:28])=[N:6][C:7]=2[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[NH:29]1[CH2:32][CH:31]([CH2:33][N:34]([CH3:40])[CH:35]2[CH2:39][CH2:38][O:37][CH2:36]2)[CH2:30]1.[C:41](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:28]([C:20]1[N:19]([C:5]2[N:4]=[C:3]3[C:8]([N:9]=[C:10]([CH2:11][N:29]4[CH2:32][CH:31]([CH2:33][N:34]([CH3:40])[CH:35]5[CH2:39][CH2:38][O:37][CH2:36]5)[CH2:30]4)[N:2]3[CH3:1])=[C:7]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:6]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=1)[CH3:41]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 59605308HCID 59605308, compoundHCID 596054202-(2-methylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

Product 1

HCID 59605905HCID 59605905, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 9-methyl-2-(2-methylbenzoimidazol-1-yl)-6-morpholin-4-yl-9H-purine-8-carbaldehyde (78 mg, 0.2 mmol), (azetidin-3-ylmethyl)methyl(tetrahydrofuran-3-yl)amine (51 mg, 0.3 mmol) and 4 Å molecular sieves (250 mg) in 1,2-dichloroethane (2 mL) was stirred at RT under nitrogen atmosphere for 6 h. Sodium triacetoxyborohydride (85 mg, 0.4 mmol) was added and the resulting reaction mixture was stirred at RT for 36 h. The solvent was reduced in vacuo and the residue was loaded onto an Isolute® SCX-2 cartridge (5 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 residue was purified by column chromatography (Si—PCC, MeOH:DCM: gradient 0:100 to 10:90) to afford 419 as a white foam (80 mg, 73%). LCMS (Method I): RT 2.05 min, [M+H]+ 546. 1H NMR (400 MHz, CDCl3): δ 7.99-7.95 (1 H, m), 7.73-7.70 (1 H, m), 7.23 (2 H, m), 4.32 (4 H, s), 3.92 (1 H, m), 3.82-3.80 (7 H, m), 3.72 (1 H, q, J=8.06 Hz), 3.61 (1 H, m), 3.51 (2 H, t, J=7.19 Hz), 3.31 (2 H, q, J=7.48 Hz), 3.08 (1 H, m), 2.95 (2 H, t, J=6.81 Hz), 2.76-2.44 (2 H, m), 2.14 (3 H, s), 2.03-1.93 (1 H, m), 1.85-1.75 (1 H, m), 1.63 (4 H, br s), 1.41 (3 H, t, J=7.48 Hz)

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at RT for 36 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
  6. customThe residue was purified by column chromatography (Si—PCC, MeOH:DCM: gradient 0:100 to 10:90)

Sources & evidence

ORD record
ord-9171d644a1de4b4cb37fb9c46f0d70a3
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…