Ammonia → (2-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-yl)methanamine

HRID 512208Notes

Reaction equation

HRID 512208 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1.N>CO.[Ni]>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 867162372-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-carbonitrile

Product 1

HCID 86716238(2-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

2-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-carbonitrile (18 mg, 0.095 mmol) was dissolved in MeOH(5 ml) and 7M NH3 in MeOH (1 ml). Argon was bubbled through the solution. Raney Nickel (6 mg, 0.1 mmol) was added and the flask was fitted with a H2-balloon and stirred at room temperature for 1½ hour. Reaction was filtred through a plug of celite and concentrated in vacuo. Used for next step without further purification. LC-MS (m/z) 194.0 (MH+), tR (minutes, Method D)=0.17.

Workup

  1. customArgon was bubbled through the solution
  2. customthe flask was fitted with a H2-balloon
  3. customReaction
  4. concentrationconcentrated in vacuo
  5. customUsed for next step without further purification

Sources & evidence

ORD record
ord-6221c7e565f74f5e8f6930fb652ed982
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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