Ammonia → HCID 86716218, compound

HRID 512190Notes

Reaction equation

HRID 512190 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:14](=O)[CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1.N.[BH3-]C#[N:20].[Na+]>CCO>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([CH:14]([NH2:20])[CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 86716219HCID 86716219, compound

Product 1

HCID 86716218HCID 86716218, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-(2-methylpyrimidin-5-yl)tetrahydro-2H-pyran-4-yl)ethanone (300 mg, 1.35 mmol), saturated NH4OAc in EtOH (15 mL) and aq.NH3 (5 mL) was added NaCNBH3 (255 mg, 4.05 mmol) and heated to reflux overnight. The EtOH was removed. The residue was extracted with EtOAc (5×10 mL) and the organic layer was discarded. The precipitation of solid was collected by filtration from the aqueous layer after 16 hours to give 1-(4-(2-methylpyrimidin-5-yl)tetrahydro-2H-pyran-4-yl)ethanamine (100 mg, yield: 33.3%). 1H NMR (DMSO-d6 400 MHz): c58.67 (s, 2H), 3.80-3.65 (m, 2H), 3.20-3.05 (m, 2H), 2.63 (s, 3H), 2.45-2.35 (m, 1H), 2.35-2.25 (m, 2H), 1.81-1.70 (m, 2H), 0.87 (d, J=6.4 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe EtOH was removed
  4. extractionThe residue was extracted with EtOAc (5×10 mL)
  5. customThe precipitation of solid
  6. filtrationwas collected by filtration from the aqueous layer after 16 hours

Sources & evidence

ORD record
ord-7c77657ef9be411c842925caed370630
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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