Hydrazine → HCID 178503377, compound

HRID 1991011Notes

Reaction equation

HRID 1991011 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][C:3]=1[C:11]1[C:22](=[O:23])[N:21]([CH3:24])[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=1.[NH2:25]N.C[N:28]([CH:30](OC)OC)C>>[CH3:24][N:21]1[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=[C:11]([C:3]2[CH:4]=[C:5]([C:6]3[NH:8][CH:30]=[N:28][N:25]=3)[CH:9]=[CH:10][C:2]=2[CH3:1])[C:22]1=[O:23]

Participants

4

Reactant 3

HCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 59128636HCID 59128636, compound

Product 1

HCID 178503377HCID 178503377, compound

Procedure

4-Methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzamide (100 mg, 0.294 mmol) was taken up in 6 mL DMFDMA, and the reaction mixture was heated to reflux for 10 minutes, then cooled and concentrated under reduced pressure. The resulting residue was taken up in 10 mL HOAc, and hydrazine (0.24 g, 7.638 mmol) was added. The reaction mixture was stirred at room temperature for 20 minutes, and the resulting precipitate was collected by filtration and washed with water to give 60 mg of 8-methyl-2-methylsulfanyl-6-[2-methyl-5-(4H-[1,2,4]triazol-3-yl)-phenyl]-8H-pyrido[2,3-d]pyrimidin-7-one, MS (M+H)=365.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 10 minutes
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-ae5e1cba60764eafa301f15a58717626
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

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