Hexane → HCID 46215810, compound

HRID 2367176Notes

Reaction equation

HRID 2367176 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][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.O.[NH2:26][NH2:27].CCOC(C)=O.CCCCCC>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][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:27][N:26]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 58504409HCID 58504409, compound

Product 1

HCID 46215810HCID 46215810, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

To 4-{2-amino-6-[(phenylmethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (367 mg, 1.15 mmol) in EtOH (10 mL) was added hydrazine monohydrate (1.0 mL, 20.4 mmol) and the reaction mixture was stirred overnight at 100° C. The mixture was poured onto water and EtOAc. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford crude product (280 mg). This material was dissolved in EtOH. Hexane was added until a precipitate began to form (a spatula was used to scratch the walls). The mixture was decanted and the solid was dried under vacuum to afford the title compound (150 mg, 39%) as a tan solid. LC-MS (ES) m/z=332 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 4.59 (s, 2H), 6.29 (s, 1H), 7.23 (m, 1H), 7.28-7.38 (m, 4H), 7.41 (d, J=8.3 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.75 (s, 1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford crude product (280 mg)
  8. customto form (a spatula
  9. customThe mixture was decanted
  10. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-c1e7a20566dc488c841f9522fc5950d7
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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