Acetic Acid → HCID 59333790, compound

HRID 1930726Notes

Reaction equation

HRID 1930726 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:17]=[C:18]([CH2:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][O:29]3)[C:19]3[CH2:25][NH:24][CH2:23][CH2:22][C:20]=3[N:21]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C=O.[C:35](O)(=O)C.C([BH3-])#N>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:17]=[C:18]([CH2:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][O:29]3)[C:19]3[CH2:25][N:24]([CH3:35])[CH2:23][CH2:22][C:20]=3[N:21]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 498716Cyano-borohydrideHCID 59333810HCID 59333810, compound

Product 1

HCID 59333790HCID 59333790, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-(2-(tetrahydrofuran-2-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.133 g, 0.31 mmol, Example 114a), formaldehyde (8.43 μL, 0.31 mmol) and acetic acid (8.76 μL, 0.15 mmol) in methanol (4 mL) was stirred at room temperature for 20 minutes. Polymer supported cyanoborohydride (0.46 g, 0.92 mmol) was added and the reaction mixture was stirred at room temperature overnight. The polymer supported cyanoborohyride was filtered off and the filtrated was purified by preparative chromatography. The product containing fractions were pooled and the solvent was evaporated. The residue was dissolved in water/acetonitrile-mixture (50:50) and freezedried giving N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-4-(2-(tetrahydrofuran-2-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.055 g, 40.1%).

Workup

  1. additionwas added
  2. filtrationwas filtered off
  3. customthe filtrated was purified by preparative chromatography
  4. additionThe product containing fractions
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in water/acetonitrile-mixture (50:50)
  7. customfreezedried

Sources & evidence

ORD record
ord-4699fb0f53f54a4db700fef44ca84de2
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

Loading…