Ammonia → 2-Isopropoxy-2-(2-methylpyrimidin-5-yl)ethanamine

HRID 512201Notes

Reaction equation

HRID 512201 reaction equation
[CH:1]([O:4][CH:5]([C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)[C:6]#[N:7])([CH3:3])[CH3:2].N>CO.[Ni]>[CH:1]([O:4][CH:5]([C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)[CH2:6][NH2:7])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 867162292-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile

Product 1

HCID 867162282-Isopropoxy-2-(2-methylpyrimidin-5-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 887MethanolSolvent2×

Procedure

2-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile (169 mg, 0.884 mmol) was dissolved in methanol (10 ml) and 7M NH3 in methanol (4 ml). Argon was bubbled through the solution for 5 minutes. To the reaction was added Raney nickel (100 mg, 1.704 mmol) and it was fitted with a H2-filled balloon. After stirring at room temperature for 20 hours LCMS shows only around 30% conversion and raney nickel (100 mg, 1.70 mmol) was added. The reaction was stirred for another 72 hours, then filtered through a plug of celite and concentrated in vacuo. The crude product used for next reaction without further purification.

Workup

  1. customArgon was bubbled through the solution for 5 minutes
  2. customwas fitted with a H2-
  3. additionfilled balloon
  4. additionwas added
  5. stirringThe reaction was stirred for another 72 hours
  6. filtrationfiltered through a plug of celite and
  7. concentrationconcentrated in vacuo
  8. customThe crude product used for next reaction without further purification

Sources & evidence

ORD record
ord-7c83b31eef824ee892e25ac7a42251da
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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