Triethylamine → 6-Chloro-N4-(3-nitrobenzyl)pyrimidine-2,4,5-triamine

HRID 732988ノート

反応式

HRID 732988 の反応式
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([NH2:10])[N:3]=1.Cl.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][NH2:19])([O-:14])=[O:13].C(N(CC)CC)C>CCCCO>[Cl:9][C:6]1[N:5]=[C:4]([NH2:10])[N:3]=[C:2]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:7]=1[NH2:8]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3010392,5-Diamino-4,6-dichloropyrimidineHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)

生成物 1

HCID 866110486-Chloro-N4-(3-nitrobenzyl)pyrimidine-2,4,5-triamine収率 78.6%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A mixture of 4,6-dichloropyrimidine-2,5-diamine (700 mg, 3.91 mmol), 3-nitrobenzylamine hydrochloride (885 mg, 4.69 mmol) and triethylamine (1.6 mL, 11.7 mmol) in n-BuOH (20 mL) was refluxed for 17 h, concentrated in vacuo and the residue partitioned between EtOAc (10 mL) and H2O (5 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound as an orange solid (906 mg, 76%) which was used in the next reaction without further purification; NMR δH (400 MHz, CDCl3) 8.16 (1H, s), 8.10 (1H, d, J 8.0 Hz), 7.80 (1H, d, J 7.5 Hz), 7.62 (1H, t, J 7.5 Hz), 7.25 (1H, t, J 6.0 Hz), 5.69 (2H, s), 4.67 (2H, d, J 6.0 Hz) and 3.93 (2H, br s).

後処理

  1. temperaturewas refluxed for 17 h
  2. concentrationconcentrated in vacuo
  3. customthe residue partitioned between EtOAc (10 mL) and H2O (5 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a16a1790f2de4b97990de2675c4e9ad8
出典データセット
uspto-grants-2009_09
特許番号
US07589097B2

反応ノート

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