HCID 178441811, compound → HCID 178441812, compound

HRID 705127Notes

Reaction equation

HRID 705127 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[O:35][CH3:36])[C:8]2[NH:13][N:12]=[C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]>C(O)C.[Pd]>[CH2:1]([C:5]1[N:6]=[C:7]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[O:35][CH3:36])[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178441811HCID 178441811, compound

Product 1

HCID 178441812HCID 178441812, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-butyl-N-(2,4-dimethoxybenzyl)-3-(6-(pyrrolidin-1-yl)hex-1-yn-1-yl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (20 g, 40.8 mmol) in ethanol (500 mL) was hydrogenated over Pd—C (5 g, 4.70 mmol) for 4 hour (H2 uptake complete). The mixture was filtered through Hyflo and evaporated. The residue in DCM (30 mL) was purified on a 120 g silica cartridge (Redisep Gold) eluted with toluene-ethanol-NH3 (85/15/1.5) in 7 batches-taking off product and lower running impurity and recycling the cartridge each time (total volume˜3 liters). Evaporation of appropriate fractions gave the title compound as a yellow gum (16.3 g).

Workup

  1. filtrationThe mixture was filtered through Hyflo
  2. customevaporated
  3. customThe residue in DCM (30 mL) was purified on a 120 g silica cartridge (Redisep Gold)
  4. washeluted with toluene-ethanol-NH3 (85/15/1.5) in 7 batches-taking off product
  5. customEvaporation of appropriate fractions

Sources & evidence

ORD record
ord-b1fc460dc9b547779a02d1c3b2dce8e2
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

Loading…