Acetic Acid → 2-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol

HRID 1930654Notes

Reaction equation

HRID 1930654 reaction equation
[CH2:1]([N:3]([CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][O:29]1)[C:4]1[C:5]2[CH2:26][NH:25][CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])=[CH:13][CH:12]=2)[N:9]=1)[CH3:2].[C:33](O)(=[O:35])[CH3:34].C(O)C=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:3]([CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][O:29]1)[C:4]1[C:5]2[CH2:26][N:25]([CH2:34][CH2:33][OH:35])[CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])=[CH:15][CH:16]=2)[N:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 756GlycolaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333811N4-Ethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Product 1

HCID 461995862-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanolYield 6.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N4-Ethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (95 mg, 0.22 mmol) was dissolved in methanol (3 mL). Acetic acid (0.013 mL, 0.22 mmol) was added followed by glycoaldehyde (13.16 mg, 0.22 mmol). The reaction was stirred at room temperature for 15 minutes and sodium cyanoborohydride (13.77 mg, 0.22 mmol) was added. The reaction was stirred for 1 h, the solvent was evaporated under reduced pressure, the crude redissolved in methanol, filtered and purified twice by preparative HPLC yielding 2-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (7.10 mg, 6.6%).

Workup

  1. stirringThe reaction was stirred for 1 h
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionthe crude redissolved in methanol
  4. filtrationfiltered
  5. custompurified twice by preparative HPLC

Sources & evidence

ORD record
ord-aa023b7652da4d9fba791b8d11ecb296
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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