Triethylamine → 1144854-41-0

HRID 2036321ノート

反応式

HRID 2036321 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.[OH:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C(N(CC)CC)C>C(O)CC>[OH:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 974724-HydroxybenzylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 53592776-Chloropurine

生成物 1

HCID 441293451144854-41-0収率 80%

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 (1478 mg) 4-hydroxybenzylamine, and 5 mL of triethylamine was refluxed in n-propanol for 3 hours. 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 diethylether. The solid residue was filtered off and the crude product crystallized from methanol. Yield 80%, white solid. TLC (EtOAc:hexane (1:1) (v:v): single spot; HPLC: purity>98%. 1H-NMR (400 MHZ, DMSO): 1.57tt (2H, Ja=11.0 Hz, Jb=3.3 Hz); 1.72qq (1H, Ja=12 Hz, Jb=3.3 Hz); 1.95tt (2H, Ja=11 Hz, Jb=2.1 Hz); 2.27qq (1H, Ja=12.0 Hz, Jb=3.3 Hz); 3.67m (1H); 4.0dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 4.6s (2H); 5.63dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 6.67d (2H, J=8.4 Hz); 7.15d (2H, J=8.4 Hz); 8.02bs (1H); 8.21s (1H); 8.33s (1H); 9.21s (1H). MS (ES): [M+H]+=326 (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 diethylether
  7. filtrationThe solid residue was filtered off
  8. customthe crude product crystallized from methanol
  9. custom4.6s (2H)
  10. custom8.21s (1H)
  11. custom8.33s (1H)
  12. custom9.21s (1H)

出典と根拠

ORDレコード
ord-ecf167ff772544f7bb83e91f7fec05b7
出典データセット
uspto-grants-2013_11
特許番号
US08575182B2

反応ノート

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