Hydrochloric Acid → 3-iodo-1-tetrahydro-1H-3-pyrrolyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride

HRID 2056201Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)[N:9]=[C:10]([I:11])[C:3]=12.[ClH:24]>CC(C)=O>[ClH:24].[I:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[NH2:1])[N:8]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[N:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of the crude tert-butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinecarboxylate in acetone (100 mL) was treated with 6 N hydrochloric acid (50 mL). The reaction mixture was stirred at 40° C. for 15 hours. The initial precipitate was filtered and confirmed by LCMS to be impurities. The reaction mixture was allowed to sit at room temperature and a precipitate formed over night. The precipitate was filtered and washed with diethyl ether. The filtration afforded 2.186 g (31%) of pure 3-iodo-1-tetrahydro-1H-3-pyrrolyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride. 1H NMR (DMSO-d6, 400 MHz) δ 9.8815 (s, 1H), 8.9923 (br.s, 1H), 8.4803 (s, 1H), 7.82 (br.s, 1H), 5.5908-5.5295 (m, 1H), 3.7131-3.6706 (m, 1H), 3.5590-3.5003 (m, 1H), 3.4466-3.4174 (m, 2H), 2.4592-2.4255 (m, 1H), 2.4064-2.3146 (m, 1H); LCMS (Thermoquest AQA single-quad MS, Genesis C18 column, 3 μm particle size, 33×4.6 mm; 70% 50 mM ammonium acetate in water to 95% acetonitrile over 6 min, 0.8 to 0.5 mL/min) Rt 1.09 min (100%), MH+ 331.0.

Workup

filtrationThe initial precipitate was filtered
customto sit at room temperature
customa precipitate formed over night
filtrationThe precipitate was filtered
washwashed with diethyl ether
filtrationThe filtration

Sources & evidence

ORD record: ord-9fcea2d6bb35436bbeca00d946aa3750
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332497B2

Reaction notes

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