Triethylamine → HCID 44582287、化合物

HRID 2422326ノート

反応式

HRID 2422326 の反応式
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.ClC1N=CN=C2C=1NC=N2.Cl.[OH:28][C:29]1[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32].C(N(CC)CC)C>C(O)CC>[OH:28][C:29]1[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 53592776-ChloropurineHCID 672424091194-90-7

生成物 1

HCID 44582287HCID 44582287、化合物収率 60%

試薬・触媒・溶媒 1

HCID 10311-Propanol溶媒

実験手順

A mixture of 10 mmol (2387 mg) 6-chloro-9-(tetrahydropyran-2-yl)purine (prepared from 10 mmol (1546 mg) of 6-chloropurine), 12 mmol (2100 mg) 2,3dihydroxybenzylamine hydrochloride, and 7 mL of triethylamine was refluxed in n-propanol for 3 hrs. After removal of the n-propanol by vacuum evaporation, the resulting material was treated with water and extracted into ethyl acetate. The ethyl acetate solvent was evaporated and the residuum subsequently washed with 30 ml of petroleum ether. The solid residue was filtered off and the crude product crystallized from methanol. Yield 60%, white solid. TLC (CHCl3:methanol) (4:1) (v:v): single spot; HPLC: purity >98%. 1H-NMR (300 MHz, DMSO): 1.57m (2H); 1.71m (1H); 1.95m (2H); 2.27qq (1H, Ja=12 Hz, Jb=4.0 Hz); 3.67m (1H); 4.00d (1H, J=11.7 Hz); 4.58bs (2H); 5.63dd (1H, Ja=11.2 Hz, Jb=1.9 Hz); 6.55tt (1H, Ja=7.7 Hz, Jb=1.5 Hz); 6.63dd (1H, Ja=7.7 Hz, Jb=1.8 Hz); 6.66dd (1H, Ja=7.7 Hz, Jb=1.8 Hz); 8.24s (1H); 8.27bs (1H); 8.37s (1H), 8.96bs (1H), 9.53bs (1H). MS (ES): [M+H]+=342 (100).

後処理

  1. customAfter removal of the n-propanol
  2. customby vacuum evaporation
  3. additionthe resulting material was treated with water
  4. extractionextracted into ethyl acetate
  5. customThe ethyl acetate solvent was evaporated
  6. washthe residuum subsequently washed with 30 ml of petroleum ether
  7. filtrationThe solid residue was filtered off
  8. customthe crude product crystallized from methanol
  9. custom8.24s (1H)
  10. custom8.37s (1H), 8.96bs (1H), 9.53bs (1H)

出典と根拠

ORDレコード
ord-496b352852474bf589e606fb410f5692
出典データセット
uspto-grants-2011_06
特許番号
US07960397B2

反応ノート

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