Ammonia → HCID 10353723, compound

HRID 646741Notes

Reaction equation

HRID 646741 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([C:15]([O:17]C)=O)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][N:8]=1.[NH3:19]>CO>[CH3:1][NH:2][C:3]1[C:4]([C:15]([NH2:19])=[O:17])=[N:5][C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68650622HCID 68650622, compound

Product 1

HCID 10353723HCID 10353723, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
82.5 °C

Procedure

A solution of of methyl 3-(methylamino)-6-phenylpyrazine-2-carboxylate (31 mg, 0.13 mmol) in methanol (5 ml) was saturated with ammonia at 0° C. The pressure tube was sealed and heated at 80-85° C. overnight. The reaction was cooled to room temperature and the solvent removed at reduced pressure to afford crude solid product. Reverse-phase BPLC purification gave 3-(methylamino)-6-phenylpyrazine-2-carboxamide (7 mg, 25% yield) as a yellow solid: 1H NM (400 MHz, CDCl3): δ 8.42 (s, 1H), 8.50 (br s, 1H), 7.90 (d, 3H), 7.45 (m, 2H), 7.40 (m, 1H), 3.10 (br s, 3H); MS (EI) for C12H12N40: 229 (MH+).

Workup

  1. customThe pressure tube was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. customthe solvent removed at reduced pressure
  4. customto afford crude solid product
  5. customReverse-phase BPLC purification

Sources & evidence

ORD record
ord-35930e1747f74d658265bbfab7c2908b
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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