Dimethylamine → Trifluoroacetic acid

HRID 2357990Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:20][CH2:21][C:22]([O:25][CH3:26])([CH3:24])[CH3:23])[N:9]=[C:10]([NH:11][C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:5]2=[CH:4][N:3]=1.C1COCC1.[CH3:32][NH:33]C.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>O1CCOCC1>[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:19])[C:12]=1[NH:11][C:10]1[C:5]2[C:6](=[N:7][C:2]([NH:33][CH3:32])=[N:3][CH:4]=2)[N:8]([CH2:20][CH2:21][C:22]([O:25][CH3:26])([CH3:23])[CH3:24])[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A sealed tube containing 55 mg (0.13 mmol) of 6-chloro-N-(2,6-dichlorophenyl)-1-(3-methoxy-3-methylbutyl)-1H-pyrazolo[3,4-d]pyrimidin-3-amine (prepared as described in Example 1, Step B), 650 μl (2.0 M, 1.3 mmol) of a THF solution of dimethylamine and 120 μl (1.6 mmol) of TFA in 3 mL 1,4-dioxane was heated at 100° C. for 21 h. After this time, 650 μl (2.0 M, 1.3 mmol) of a THF solution of dimethylamine and 120 μl (1.6 mmol) of TFA were added, and heating was continued at 100° C. for an additional 23 h. The orange solution was concentrated, and the residue was purified by HPLC (Capcell Pak C18 5 μm, gradient of 80% A:20% B to 30% A:70% B over 45 min; A=0.5% TFA in water, B=0.5% TFA in acetonitrile) to give the title compound. 1H-NMR (CDCl3) δ 1.25 (s, 6H), 2.01-2.08 (m, 2H), 3.05 (s, 3H), 3.22 (s, 3H), 4.19-4.26 (m, 2H), 6.60 (s, 1H), 7.24 (t, J=8.4 Hz, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.77 (s, 1H), 9.49 (s, 1H). Mass Spectrum (ESI) m/e=409.1.

Workup

temperatureheating
concentrationThe orange solution was concentrated
customthe residue was purified by HPLC (Capcell Pak C18 5 μm, gradient of 80% A
wait20% B to 30% A:70% B over 45 min

Sources & evidence

ORD record: ord-e16b98d04826478fb650e4642f264cfb
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763624B2

Reaction notes

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