Trifluoroacetic acid → 5-chloro-N2-(1,3-dimethyl-1H-pyrazol-4-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl) pyrimidine-2,4-diamine

HRID 1478078Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.Cl.[CH3:26][N:27]1[CH:31]=[C:30]([NH2:32])[C:29]([CH3:33])=[N:28]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:10][CH:11]3[CH2:15][NH:14][CH2:13][CH:12]3[CH2:23]2)=[N:7][C:2]([NH:32][C:30]2[C:29]([CH3:33])=[N:28][N:27]([CH3:26])[CH:31]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole2(1H)-carboxylate (573.1 mg, 1.54 mmol) and 1,3-dimethylpyrazol-4-amine hydrochloride (458.8 mg, 3.11 mmol) in dioxane (10 mL) was added trifluoroacetic acid (856.4 mg, 7.51 mmol). The reaction mixture was stirred at 100° C. overnight and adjusted to pH=10 with a saturated Na2CO3 solution, then extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM=1/10) to give the title compound as a beige solid (256.8 mg, 48.1%).

Workup

extractionextracted with DCM (100 mL×3)
washThe combined organic phases were washed with brine (100 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM=1/10)

Sources & evidence

ORD record: ord-2ad1c6b944364b49b9bd520d84584e0c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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