Pyridine → 4-[2-Amino-6-(tetrahydro-furan-3-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1020765ノート

反応式

HRID 1020765 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][O:10][CH2:9]2)[N:5]=[C:4]([NH2:13])[N:3]=1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].N1C=CC=CC=1>CCO>[C:17]([O:16][C:14]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:7]=[C:6]([CH:8]3[CH2:12][CH2:11][O:10][CH2:9]3)[N:5]=[C:4]([NH2:13])[N:3]=2)[CH2:23][CH2:22]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

参加物

5

反応物 3

HCID 1049PyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 866223774-Chloro-6-(tetrahydro-furan-3-yl)-pyrimidin-2-ylamine

生成物 1

HCID 670962764-[2-Amino-6-(tetrahydro-furan-3-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester収率 14.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 4-chloro-6-(tetrahydro-furan-3-yl)-pyrimidin-2-ylamine (500 mg, 2.51 mmol), N-BOC piperazine (960 mg, 5.15 mmol) and pyridine (500 uL, 6.1 mmol) in EtOH (10 mL) was heated at 90° C. for 4 h. Upon cooling to rt a thick precipitate formed which was collected by filtration. The material was rinsed with EtOAc to afford 125 mg of a white solid. The filtrate was concentrated and triturated with Et2O-EtOAc (1:1) to yield an additional 600 mg of material (82% combined). MS (ESI): mass calcd. for C17H27N5O3, 349.2; m/z found, 350.3 [M+H]+. 1H NMR (CDCl3): 5.86 (s, 1H), 4.70 (br s, 2H), 3.90-4.07 (m, 2H), 3.83-3.90 (m, 2H), 3.55-3.60 (m, 4H), 3.45-3.50 (m, 4H), 3.18-3.26 (m, 1H), 2.20-2.30 (m, 1H), 2.09-2.18 (m, 1H), 1.48 (s, 9H).

後処理

  1. customformed which
  2. filtrationwas collected by filtration
  3. washThe material was rinsed with EtOAc

出典と根拠

ORDレコード
ord-98787def5704417093c6d1959b0cba2f
出典データセット
uspto-grants-2014_05
特許番号
US08716475B2

反応ノート

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