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

HRID 1192300ノート

反応式

HRID 1192300 の反応式
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]

参加物

4

反応物 2

HCID 67540580HCID 67540580、化合物HCID 178418922HCID 178418922、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0cb683e6150489f9ea853653a5824bb
出典データセット
uspto-grants-2014_03
特許番号
US08680114B2

反応ノート

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