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

HRID 2056201ノート

反応式

HRID 2056201 の反応式
[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

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 22346849HCID 22346849、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9fcea2d6bb35436bbeca00d946aa3750
出典データセット
uspto-grants-2008_02
特許番号
US07332497B2

反応ノート

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