Hydrazine hydrate (1:1) → HCID 22346624, compound

HRID 897398Notes

Reaction equation

[CH3:1][C:2]([NH:10][C:11]1[N:16]=[C:15](Cl)[C:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:13]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:12]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].O.[NH2:32][NH2:33]>C(O)(C)C>[CH3:1][C:2]([NH:10][C:11]1[N:16]=[C:15]([NH:32][NH2:33])[C:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:13]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:12]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

2-((1-methyl-1-phenylethyl)amino)-4-chloro-5-(4-fluorophenyl)-6-(4-pyridyl)pyrimidine (218 mg, 0.52 mmol) was combined with a solution of hydrazine hydrate (130 mg 2.60 mmol) and isopropylalcohol (ca. 10 mL). The mixture was heated at 70° C. for 4 h. The reaction was cooled to RT, the solvent was evaporated in vacuo and the residue was purified by flash chromatography (2% MeOH:CHCl3) to provide the product as an off-white solid; MS m/z (M+H)+ 415; C24H23FN6 requir. 414.5.

Workup

temperatureThe reaction was cooled to RT
customthe solvent was evaporated in vacuo
customthe residue was purified by flash chromatography (2% MeOH:CHCl3)

Sources & evidence

ORD record: ord-ab0d2bfce8db481e8f68fbfc46f01474
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921762B2

Reaction notes

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