HCID 67540580, 화합물 → tert-Butyl 4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)piperazine-1-carboxylate

HRID 1192300노트

반응식

HRID 1192300 반응식
C(O[K])(C)(C)C.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:25]([NH2:26])=[C:24]([C:27]#[C:28][Si](C)(C)C)[N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CN1C(=O)CCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:25]3[NH:26][CH:28]=[CH:27][C:24]=3[N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

참가 물질

4

반응물 2

HCID 67540580HCID 67540580, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

HCID 67539894tert-Butyl 4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)piperazine-1-carboxylate수율 53%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

To a solution of tBuOK (0.063 g, 0.56 mmol) in NMP (4 mL) was added 4-(5-Amino-6-trimethylsilanylethynyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.1 g, 0.27 mmol) in NMP (1 mL) under N2. The mixture was vigorously stirred at room temperature for 4 hours. The reaction was quenched with water (1 mL) and ethyl acetate (50 mL). The organic phase was washed brine and water until NMP was gone, then dried over MgSO4, filtered and concentrated. The residue was subject to chromatography on silica gel to afford the product 4-(5H-Pyrrolo[3,2-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (43 mg, 53%). 1H NMR (CDCl3, 400 Hz) δ 9.47 (s, 1H), 8.49 (s, 1H), 7.37 (d, J=2.4 Hz, 1H), 6.62 (d, J=2.8 Hz, 1H), 3.85-3.82 (m, 4H), 3.61-3.58 (m, 4H). 1.49 (s, 9H). MS (ESI+) [M+H]+ 304.

후처리

  1. customThe reaction was quenched with water (1 mL) and ethyl acetate (50 mL)
  2. washThe organic phase was washed brine and water until NMP
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c0cb683e6150489f9ea853653a5824bb
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680114B2

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