Chloroform → HCID 178506016、化合物

HRID 81442ノート

反応式

HRID 81442 の反応式
Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.CCN(C(C)C)C(C)C.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH2:28])[CH:22]=1.C(Cl)(Cl)Cl>CCCCO.CO>[F:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][NH:6]2)=[C:2]([NH:28][CH2:27][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)[N:10]=1

参加物

7

反応物 4

HCID 6212ChloroformHCID 310183-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 52879146-Chloro-2-fluoropurine

生成物 1

HCID 178506016HCID 178506016、化合物

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 887Methanol溶媒

反応条件

温度
-20 °C

実験手順

To a stirred solution of 6-chloro-2-fluoropurine (0.9 g, 1 eq, 5.22 mmol) in n-BuOH (60 mL) under an argon atmosphere, cooled to −20° C., was added DIEA (2.5 mL, 2.75 eq, 14.35 mmol) followed by C-pyridin-3-yl-methylamine (0.58 mL, 1.1 eq, 5.69 mmol). The reaction mixture was stirred at −20° C. for 3 h, and then allowed to return to room temperature over 2 h, when TLC (CHCl3:MeOH; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue was purified by gradient column chromatography on silica gel, eluted with CHCl3:MeOH (97:3→90:10), to afford the title compound as a white solid. Yield: 1.08 g (85%). Mp 218-220° C. 1H-NMR (d6-DMSO, 250 MHz): δ 4.65 (d, 2H, J=5.37 Hz, —HNCH2-Pyr), 7.34, 8.43, 8.57 (3×m, 4H, Pyr), 8.10 (s, 1H, —N═CH—NH—), 8.83 (bs, 1H, —HNCH2-Pyr), 13.07 (bs, 1H, —N═CH—NH—). FABMS m/z (relative intensity): 245 ([M+H]+, 40), 176 (27), 154 (100), 136 (74). Accurate Mass (M+H): Actual: 245.0951, Measured: 245.0942. Microanalysis (Expected: Measured) C11H9N6F.0.2H2O: C, 53.31; 54.03; H, 3.82; 3.83; N, 33.91; 32.74.

後処理

  1. waitto return to room temperature over 2 h
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by gradient column chromatography on silica gel
  4. washeluted with CHCl3:MeOH (97:3→90:10)

出典と根拠

ORDレコード
ord-0efa2b849d624da4a9a403f5dcfda937
出典データセット
uspto-grants-2014_09
特許番号
US08846696B2

反応ノート

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