Formaldehyde → HCID 73297209, compound

HRID 592419Notes

Reaction equation

HRID 592419 reaction equation
C=O.[Cl:3][C:4]1[C:5]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]([CH3:35])[C:32]([NH2:34])=[O:33])=[N:6][C:7]([NH:10][C:11]2[CH:12]=[N:13][C:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:15][CH:16]=2)=[N:8][CH:9]=1.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[Cl:3][C:4]1[C:5]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]([CH3:35])[C:32]([NH2:34])=[O:33])=[N:6][C:7]([NH:10][C:11]2[CH:12]=[N:13][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([CH3:36])[CH2:19][CH2:18]3)=[CH:15][CH:16]=2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 73297208HCID 73297208, compound

Product 1

HCID 73297209HCID 73297209, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde (31.2 μL, 0.419 mmol, 37 wt % in H2O) was added to a suspension of 2-(2-(2-(5-chloro-2-((6-(piperidin-4-yl)pyridin-3-yl)amino)pyrimidin-4-yl)ethyl)phenyl)propanamide 37 (39.0 mg, 0.084 mmol) in MeOH (2.0 mL) under an atmosphere of nitrogen. Sodium triacetoxyborohydride (178 mg, 0.839 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 2.5 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (10 mL) and sat. aq. NaHCO3 (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with water (20 mL) and brine (15 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting solid was suspended in DCM (20 mL) and cyclohexane (30 mL). The solid was filtered to give the title compound 38 (34 mg, 84%). LCMS-C: rt 4.19 min; m/z 479.2 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was diluted with EtOAc (10 mL) and sat. aq. NaHCO3 (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  5. washThe combined organic layers were washed with water (20 mL) and brine (15 mL)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-55d0cba24e3544a0b7427d199ca881fe
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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