Methylhydrazine → HCID 86629377, compound

HRID 1093215Notes

Reaction equation

HRID 1093215 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH:9]=O)=[C:4](Cl)[N:3]=1.[CH3:12][NH:13][NH2:14].C(N(CC)CC)C.Cl.[CH:23]12[O:30][CH:27]([CH2:28][CH2:29]1)[CH2:26][NH:25][CH2:24]2>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]2[N:13]([CH3:12])[N:14]=[CH:9][C:5]2=[C:6]([N:25]2[CH2:24][CH:23]3[O:30][CH:27]([CH2:28][CH2:29]3)[CH2:26]2)[N:7]=1

Participants

6

Reactant 4

HCID 6061MethylhydrazineHCID 8471TriethylamineHCID 109327462,4,6-Trichloro-5-pyrimidinecarboxaldehydeHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

Product 1

HCID 86629377HCID 86629377, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cloudy solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (1.1 g, 5.2 mmol) in chloroform (50 mL) cooled to −78° C. was added in drops methylhydrazine (0.24 g, 5.2 mmol), followed by triethylamine (1.4 mL). The cooling bath was then removed, allowing the mixture to warm to room temperature. The mixture was concentrated to dryness under reduced pressure, and the residue was dissolved in ethanol (50 mL). Triethylamine (1 mL) was added to the mixture, followed by 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.51 g, 3.4 mmol). The mixture was concentrated under reduced pressure and the residue was purified by automated flash chromatography (methanol/chloroform) to provide 3-(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. MS (ES+): 280.0, 281.9 (M+H)+

Workup

  1. customThe cooling bath was then removed
  2. concentrationThe mixture was concentrated to dryness under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (50 mL)
  4. additionTriethylamine (1 mL) was added to the mixture
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue was purified by automated flash chromatography (methanol/chloroform)

Sources & evidence

ORD record
ord-04ab4e5fa5d04a5787fb3f15d237f6ae
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

Loading…