Triphenylphosphine → 1-(3-bromopropyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2056193ノート

反応式

HRID 2056193 の反応式
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[Br:12][CH2:13][CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:12][CH2:13][CH2:14][CH2:15][N:4]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]2[C:2]([I:1])=[N:3]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 178508725HCID 178508725、化合物

生成物 1

HCID 223466991-(3-bromopropyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10.00 g, 38.31 mmol) in tetrahydrofuran (150 mL) was treated with 3-bromo-1-propanol (15.98 g, 114.93 mmol) and triphenylphosphine (20.1 g, 76.62 mmol). Diethylazodicarboxyate (13.34 g, 76.62 mmol) was slowly added to the reaction mixture. The reaction mixture was stirred at 0° C. for 30 min, after which the ice bath was removed and was stirred for 30 minutes at room temperature. The reaction mixture was partially concentrated and ethyl acetate (200 mL) was added. The precipitate was filtered and the filtrate was concentrated to dryness. The crude compound was purified by flash chromatography on silica gel using 100% ethyl acetate as the eluent. The afforded 7.8 g (53%) of 1-(3-bromopropyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (DMSO-d6, 400 MHz) δ 8.230 (s, 1H), 4.419-4.385 (t, 2H), 3.530-3.498 (t, 2H), 2.370-2.304 (q, 2H); 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 2.05 min (100%), MH+ 422.9.

後処理

  1. customafter which the ice bath was removed
  2. stirringwas stirred for 30 minutes at room temperature
  3. concentrationThe reaction mixture was partially concentrated
  4. additionethyl acetate (200 mL) was added
  5. filtrationThe precipitate was filtered
  6. concentrationthe filtrate was concentrated to dryness
  7. customThe crude compound was purified by flash chromatography on silica gel using 100% ethyl acetate as the eluent
  8. customLCMS (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 2.05 min (100%), MH+ 422.9

出典と根拠

ORDレコード
ord-abbe699b87084c06b147ee77e2db3dda
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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