Formaldehyde → 1-(2-(2-(5-Methyl-2-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592439Notes

Reaction equation

HRID 592439 reaction equation
[CH3:1][C:2]1[C:3]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2([C:31]([NH2:33])=[O:32])[CH2:30][CH2:29]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:13]=2)=[N:6][CH:7]=1.C=O.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][C:2]1[C:3]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2([C:31]([NH2:33])=[O:32])[CH2:29][CH2:30]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17]([CH3:36])[CH2:16][CH2:15]3)[CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 867123181-(2-(2-(5-Methyl-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Product 1

HCID 732949441-(2-(2-(5-Methyl-2-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-(2-(5-methyl-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A44 (0.064 g, 0.14 mmol) in MeOH (12 mL) was added formaldehyde solution (37% in water, 32 μL, 0.43 mmol) and sodium triacetoxyborohydride (0.122 g, 0.575 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature for 4 hours before concentrating under reduced pressure. The mixture was diluted with sat. aq. NaHCO3 (20 mL) and the aqueous phase was extracted with EtOAc (3×25 mL). The combined organics were washed with brine, and dried (MgSO4) before the solvent was removed in vacuo to give the title compound 48 as a white solid (0.035 g, 53%). LCMS-D: rt 2.89 min; m/z 460 [M+H]+.

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. additionThe mixture was diluted with sat. aq. NaHCO3 (20 mL)
  3. extractionthe aqueous phase was extracted with EtOAc (3×25 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4) before the solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-d4fefa8a2e94404dbf1b98ce8e6b2a42
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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