Hydrazinium chloride → 2-methylsulfanyl-4-(1H-pyrazol-5-yl)pyrimidine

HRID 2214786Notes

Reaction equation

HRID 2214786 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1)=O.Cl.[NH2:17]N>C(O)C>[CH3:14][S:13][C:9]1[N:8]=[C:7]([C:5]2[NH:17][N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 21948442(E)-3-(dimethylamino)-1-(2-(methylthio)pyrimidin-4-yl)prop-2-en-1-one

Product 1

HCID 219484812-methylsulfanyl-4-(1H-pyrazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2E)-3-(dimethylamino)-1-[2-(methylthio)pyrimidin-4-yl]prop-2-en-1-one (1-4, 1.0 g, 4.48 mmol, 1 equiv) and hydrazine hydrochloride (0.62 g, 8.96 mmol, 2 equiv) in ethanol(20 mL) was heated at reflux for 20 hours. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate(2×50 mL) and sat. sodium bicarbonate solution. The combined organic extracts were dried over magnesium sulfate and concentrated to a solid which was triturated with ether to provide 2-(methylthio)-4-(1H-pyrazol-5-yl)pyrimidine (4-1) as a tan solid. 1H NMR (500 MHz, CDCl3) δ 10.8 (br s, 1H), 8.55 (d, 1H, J=5 Hz), 7.68 (d, 1H, J=5 Hz), 7.40 (br s, 1H), 6.96 (br s, 1H), 2.63 (s, 3H).

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate(2×50 mL) and sat. sodium bicarbonate solution
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated to a solid which
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-7cdb90d01afa4e60badf6455fb946cad
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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