Methylhydrazine → HCID 86700470, compound

HRID 879657Notes

Reaction equation

HRID 879657 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)=O)[CH:7]=1.[CH3:17][NH:18][NH2:19]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:18]([CH3:17])[N:19]=[C:8]2[C:10]1[CH:11]=[N:12][CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 86700469HCID 86700469, compound

Product 1

HCID 86700470HCID 86700470, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A heavy wall pressure flask was charged with (5-bromo-2-fluorophenyl)(pyrimidin-5-yl)methanone (2.08 g, 7.4 mmol) and dioxane (20 mL). Methylhydrazine (0.86 mL, 16.3 mmol) was then added, and the mixture was heated to 100° C. for 16 hours. The crude mixture was concentrated, and the residue suspended in DCM. After storing at −10° C. for 2 hours, the precipitated solids were filtered off to give the product. 1H NMR (400 MHz, DMSO-d6) δ 9.35 (s, 2H), 9.22 (s, 1H), 8.39 (d, J=1.1 Hz, 1H), 7.76 (d, J=8.9 Hz, 1H), 7.62 (dd, J=8.9, 1.7 Hz, 1H), 4.15 (s, 3H).

Workup

  1. concentrationThe crude mixture was concentrated
  2. filtrationthe precipitated solids were filtered off
  3. customto give the product

Sources & evidence

ORD record
ord-17d509eb1ac24975a221ab0c3e27ef57
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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