Triethyl phosphite → HCID 14284086, compound

HRID 1184867Notes

Reaction equation

HRID 1184867 reaction equation
P(OCC)(OCC)OCC.[NH2:11][C:12]1[C:17]([C:18]#[N:19])=[N:16][C:15]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[CH:14][N+:13]=1[O-]>O>[NH2:11][C:12]1[C:17]([C:18]#[N:19])=[N:16][C:15]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 178510567HCID 178510567, compound

Product 1

HCID 14284086HCID 14284086, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

triethyl phosphite (20 mL, 19.20 g, 116 mmol) was heated to 130° C. and 2-amino-3-cyano-5-(furan-2-yl)pyrazine 1-oxide 55 (3.37 g, 13.34 mmol) was added in portions (±20 min). The reaction was stirred for 1 h, cooled down to 70° C., water (40 mL) was added and stirred for 30 min at 70° C. Cooled down with ice bad and the resulting precipitate was collected, washed with water and dried to give 3-amino-6-(furan-2-yl)pyrazine-2-carbonitrile 56 (2.46 g, 99%). NMR (400 MHz, DMSO-d6) 6.64 (m, 1H), 6.99 (d, J=3.5 Hz, 1H), 7.51 (br s, 1H), 7.80 (m, 1H), 8.70 (s, 1H). (m/z)=187 (M+H)+.

Workup

  1. stirringstirred for 30 min at 70° C
  2. temperatureCooled down with ice bad
  3. customthe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-78db77cfb0024fdda87dc3e4cc53c697
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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