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

HRID 723430

반응식

HRID 723430 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cb33c0f8c8b24b3da04a480ad70e26d4
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141575B2

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