tert-Butanol → tert-Butyl (5-methylpyrazin-2-yl)carbamate

HRID 1821737노트

반응식

HRID 1821737 반응식
C[C:2]1[N:3]=[CH:4][C:5]([C:8](O)=O)=[N:6][CH:7]=1.C([N:13]([CH2:16]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[CH3:35][C:36]([OH:39])([CH3:38])[CH3:37]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:36]([O:39][C:16](=[O:25])[NH:13][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1)([CH3:38])([CH3:37])[CH3:35]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 199401P,P-Diphenylphosphinic azide

생성물 1

HCID 22046506tert-Butyl (5-methylpyrazin-2-yl)carbamate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 5-methyl pyrazine carboxylic acid (13.8 g, 100 mmol) in 300 mL of toluene at room temperature under nitrogen was added triethyl amine (14 mL, 100 mmol) followed by diphenyl phosphoryl azide (21.6 mL, 100 mmol). After 30 min. at room temperature, 2-methyl-2-propanol (19 mL, 200 mmol) was added and the solution immersed in a 90° C. oil bath. After 2 hours, the reaction was cooled to RT, diluted to 600 mL with EtOAc, and washed 3×60 mL with 10% Na2CO3 and 1×600 mL with saturated NaCl. The organics were dried (MgSO4), filtered and concentrated to a yellow solid (17.5 g. 83%). 1H-NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 8.05 (s, 1H), 7.56(br s, 1H), 2.50 (s, 3H), 1.55 (s, 9H).

후처리

  1. customimmersed in a 90° C.
  2. waitAfter 2 hours
  3. washwashed 3×60 mL with 10% Na2CO3 and 1×600 mL with saturated NaCl
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid (17.5 g. 83%)

출처 및 근거

ORD 기록
ord-6fd05748a38b4fe1b55f702617f381f2
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608618B2

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