Hydrazine hydrate (1:1) → HCID 51356854, compound

HRID 2367185Notes

Reaction equation

HRID 2367185 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]([NH:17][CH:18]([CH3:20])[CH3:19])[N:3]=1.O.[NH2:22][NH2:23]>CCO>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][CH:18]([CH3:20])[CH3:19])[CH:5]=3)=[CH:15][CH:14]=2)[NH:23][N:22]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 51356587HCID 51356587, compound

Product 1

HCID 51356854HCID 51356854, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

In a 25 mL sealable tube were combined 4-{2-amino-6-[(1-methylethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (0.21 g, 0.54 mmol), hydrazine monohydrate (1.06 mL, 21.6 mmol), and EtOH (10 mL). The tube was sealed and the reaction mixture was stirred overnight at 95° C. The mixture was concentrated and to the resulting solid was added to EtOH (2 mL) followed by hexanes (15 mL). The mixture was sonicated and filtered. The solid was washed with hexanes to afford the title compound (167 mg, 99%) as an off-white solid. LC-MS (ES) m/z=284 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.15 (d, J=6.6 Hz, 6H), 4.12 (bs, 1H), 5.36 (s, 2H), 5.94 (s, 2H), 6.24 (s, 1H), 6.71 (d, J=7.6 Hz, 1H), 7.40 (d, J=8.6 Hz, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.82 (s, 1H), 11.50 (bs, 1H).

Workup

  1. customIn a 25 mL sealable tube were combined
  2. customThe tube was sealed
  3. concentrationThe mixture was concentrated and to the resulting solid
  4. additionwas added to EtOH (2 mL)
  5. customThe mixture was sonicated
  6. filtrationfiltered
  7. washThe solid was washed with hexanes

Sources & evidence

ORD record
ord-6bfe30d58a24495eaed7ec86c4c0877d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…