1-((6-Fluoropyridin-2-yl)methyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine → N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine

HRID 594983Notes

Reaction equation

FC1N=C(C[N:9]2[C:13]3=[N:14][C:15]([NH:18][C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[N:16][CH:17]=[C:12]3[CH:11]=[N:10]2)C=CC=1>CN(C=O)C>[CH3:24][N:22]1[CH:23]=[C:19]([NH:18][C:15]2[N:14]=[C:13]3[NH:9][N:10]=[CH:11][C:12]3=[CH:17][N:16]=2)[CH:20]=[N:21]1

Participants

Conditions

Temperature: 180 °C

Procedure

1-((6-fluoropyridin-2-yl)methyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (Example 170) (45 mg, 0.138 mmol) was dissolved in DMF (0.6 ml) in a microwave tube under Nitrogen. This was sealed and heated at 180° C. for 1 h. The mixture was concentrated and purified by prep HPLC to afford 1-46-(dimethylamino)pyridin-2-yl)methyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine as yellowish solid (20 mg, 42% yield). 1H NMR (d6-Acetone) δ 8.88 (s and br s, 2H), 8.06 (s, 1H), 7.99 (s, 1H), 7.61 (s, 1H), 7.40 (t, 1H), 6.49 (d, 1H), 6.24 (br s, 1H), 5.51 (s, 2H), 3.83 (s, 3H), 3.02 (s, 6H); LC-MS method B, (ES+) 350.1, RT=5.06 min.

Workup

customThis was sealed
concentrationThe mixture was concentrated
custompurified by prep HPLC

Sources & evidence

ORD record: ord-2b66b25df2ab4933a8c5684071d20c95
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242987B2

Reaction notes

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