Hydrazine hydrate (1:1) → HCID 46214481, compound

HRID 2367198Notes

Reaction equation

HRID 2367198 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.O.[NH2:24][NH2:25]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:24][NH:25]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 51356584HCID 51356584, compound

Product 1

HCID 46214481HCID 46214481, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Into a 25 mL sealable tube under argon were added 4-(2-amino-6-phenyl-4-pyrimidinyl)-2-fluorobenzonitrile (0.052 g, 0.18 mmol) and EtOH (5 mL). Hydrazine monohydrate (0.35 mL, 7.17 mmol) was added, the vial was sealed, and the reaction mixture was stirred overnight at 95° C. The reaction was cooled to room temperature and concentrated. The resulting solid was sonicated in a mixture of EtOH (1 mL) and water (10 mL), filtered, washed with water, and dried under vacuum at 40° C. to afford the title compound as a yellow solid (44 mg, 77%). LC-MS (ES) m/z=303 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 5.43 (s, 2H), 6.74 (s, 2H), 7.46-7.59 (m, 3H), 7.69-7.84 (m, 3H), 8.12 (s, 1H), 8.23 (m, 2H), 11.63 (s, 1H).

Workup

  1. customthe vial was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. customThe resulting solid was sonicated in a mixture of EtOH (1 mL) and water (10 mL)
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-7f63d9ef777e490ab4312d1413cbb500
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…