Sodium borohydride → 5-(2-(Hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)picolinonitrile

HRID 1772713Notes

Reaction equation

HRID 1772713 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=3)[N:6]2[CH:25]=1)=[O:2].[BH4-].[Na+]>CO.O>[OH:2][CH2:1][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=3)[N:6]2[CH:25]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1177284605-(2-Formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)picolinonitrile

Product 1

HCID 1177279105-(2-(Hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)picolinonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Compound 75a (74.5 mg, 0.223 mmol) was suspended in MeOH (10 mL) and then NaBH4 (26.3 mg, 0.695 mmol) was added. The reaction was stirred at rt for 18 h and then diluted with water (10 mL) and filtered. The solid was collected by filtration and the filter cake was washed with water (2×10 mL). The solid was dissolved in a mixture of DCM (100 mL) and MeOH (50 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to afford compound 75b. 1H-NMR (400 MHz, CD3OD+CDCl3) δ (ppm): 8.96 (d, J=2.2 Hz, 1H), 8.20 (dd, J=8.1, 2.2 Hz, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.70 (s, 1H), 7.43 (s, 1H), 4.79 (s, 2H), 4.29-4.36 (m, 4H), 3.85-3.94 (m, 4H). LCMS calcd for C17H16N6O2: 337.1 (M+H). found: 337.1.

Workup

  1. filtrationfiltered
  2. filtrationThe solid was collected by filtration
  3. washthe filter cake was washed with water (2×10 mL)
  4. dissolutionThe solid was dissolved in a mixture of DCM (100 mL) and MeOH (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-62e87d7bc6764a15a11438947f7ed5c1
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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