Acetic Acid → HCID 46198655, compound

HRID 1930583Notes

Reaction equation

HRID 1930583 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:25][CH2:26][OH:27])[C:17]4[CH2:23][NH:22][CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[N:3]1.[C:34](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:34][N:22]1[CH2:21][CH2:20][C:18]2[N:19]=[C:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[CH:12][CH:11]=3)[N:15]=[C:16]([N:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:25][CH2:26][OH:27])[C:17]=2[CH2:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333755HCID 59333755, compound

Product 1

HCID 46198655HCID 46198655, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-((2-(4-(1-Methyl-1H-pyrazol-4-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (40 mg, 0.09 mmol) was dissolved in methanol (2 mL). Acetic acid (1.037 μL, 0.02 mmol) was added followed by formaldehyde (0.014 mL, 0.18 mmol). The reaction mixture was stirred at room temperature for 30 minutes before sodium cyanoborohydride (11.39 mg, 0.18 mmol) was added. After 20 minutes the solvent was evaporated under reduced pressure, the crude dissolved in few drops of DMF and acetonitrile, filtered and purified by preparative HPLC yielding 2-((6-methyl-2-(4-(1-methyl-1H-pyrazol-4-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (9.8 mg, 21%) as acetic acid salt. MS (ESI) (M+H) m/z 456;

Workup

  1. additionwas added
  2. customAfter 20 minutes the solvent was evaporated under reduced pressure
  3. dissolutionthe crude dissolved in few drops of DMF and acetonitrile
  4. filtrationfiltered
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-edc8a28ece1042f49a09ff45f830b2a0
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

Loading…