Methylamine → (2-Chloro-9-fluoro-3-phenylpyrimido[1,2-b]indazol-4-yl)methylamine

HRID 877056Notes

Reaction equation

[Cl:1][C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14](Cl)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1.[CH3:23][NH2:24]>O1CCCC1.CN(C)C=O>[Cl:1][C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([CH2:23][NH2:24])[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2 g (7.5 mmol) 2,4-Dichloro-9-fluoro-3-phenylpyrimido[1,2-b]indazole (intermediate example Int-1-0, step 2) and 7.5 mL (15 mmol) of a 2M solution of methylamine in tetrahydrofuran were dissolved in 16.8 mL N,N-dimethylformamide and heated in the microwave for 20′ at 100° C. The solvent was evaporated and the residue was purified by chromatography on silicagel (eluents: dichloromethane/methanol) yielding 960 mg (46.4%) of the desired compound.

Workup

customThe solvent was evaporated
customthe residue was purified by chromatography on silicagel (eluents: dichloromethane/methanol)

Sources & evidence

ORD record: ord-b2b4cd7a53814c59a5f6d6fb12a98348
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987286B2

Reaction notes

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