Hydrochloric Acid → N-{3-[2-(2-Aminopyridin-4-yl)ethyl]phenyl}-2-chloro-5-fluoropyrimidin-4-amine Dihydrochloride

HRID 541856Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23]C(=O)OC(C)(C)C)[CH:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([F:31])=[CH:4][N:3]=1.[ClH:32]>O1CCOCC1>[ClH:1].[ClH:32].[NH2:23][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C:11]2[CH:10]=[C:9]([NH:8][C:6]3[C:5]([F:31])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:14]=[CH:13][CH:12]=2)[CH:22]=[CH:21][N:20]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of tert-butyl [4-(2-{3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-2-yl]carbamate (88 mg, 0.20 mmol) in 1,4-dioxane (0.50 mL) was added 4 M hydrogen chloride in 1,4-dioxane (2.0 mL). The resultant reaction mixture was stirred at 40° C. for 1 hour. The reaction mixture was concentrated under vacuum to give the desired product as a very hygroscopic white powder (83 mg, 100%). LCMS for C17H16ClFN5 (M+H)+: m/z=344.1.

Workup

customThe resultant reaction mixture
concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-7738fd2088b54f42abaaa30df76b2a4e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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