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

HRID 898026노트

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HRID 898026 반응식
[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

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 22346849HCID 22346849, 화합물

생성물 1

HCID 223473313-iodo-1-tetrahydro-1H-3-pyrrolyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride수율 31%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  1. filtrationThe initial precipitate was filtered
  2. customto sit at room temperature
  3. customa precipitate formed over night
  4. filtrationThe precipitate was filtered
  5. washwashed with diethyl ether
  6. filtrationThe filtration

출처 및 근거

ORD 기록
ord-dd85a10daff843fb96de7a6a77e461a2
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921763B2

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