Triethylamine → Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

HRID 2401444

반응식

HRID 2401444 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5](Br)=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[H][H]>[Pd].C(OCC)(=O)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 86649359Tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 68602141Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21584119Ethylacetate methanol용매

실험 절차

A solution of tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamate (Example 1A, 18.60 g, 0.0507 mole), triethylamine (135.0 mL, 0.9686 mole), and 10% palladium on charcoal (7.40 g) in 1:1 ethyl acetate/methanol (500 mL) was treated with hydrogen (60 psi) for two days. Insoluble material was removed by filtration through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate as a white, amorphous solid (12.7 g, 98.8% yield). 1H NMR (300 MHz, CD3Cl3) δ ppm 1.44 (s, 9H), 3.27-3.37 (m, 2H), 3.37-3.47 (m, 2H), 5.00 (sbr, 2H), 5.28 (sbr, 1H), 5.52 (sbr, 1H), 5.78 (d, J=6 Hz, 1H), 7.76 (d, J=6 Hz, 1H). MS (DCl—NH3) m/z=254 (M+H)+.

후처리

  1. customInsoluble material was removed by filtration through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-67d771c486544bfb8e850714a9ea605b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796297B2

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