Aniline → 4-methoxy-N-phenylpyrimidin-2-amine

HRID 1676387ノート

反応式

HRID 1676387 の反応式
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

参加物

5

反応物 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 5889352-Chloro-4-methoxypyrimidine

生成物 1

HCID 156155044-methoxy-N-phenylpyrimidin-2-amine収率 11.8%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
100 °C

実験手順

A sealed tube was charged with 2-chloro-4-methoxypyrimidine (1.00 g, 6.92 mmol) in 2-propanol (5 mL). Aniline (0.757 ml, 8.30 mmol) and DIEA (1.45 ml, 8.30 mmol) were added and the reaction mixture was heated at 100° C. until the reaction was complete by HPLC. The reaction mixture was cooled to room temperature. The resulting thick suspension was filtered, washed with ethanol, collected and dried under vacuum to yield the desired product (0.164 g) as a white solid. The filtrate was concentrated and then partitioned between EtOAc and saturated aqueous NaCl. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a yellow solid. The crude product was purified by flash column chromatography, eluting with 25:1 dichloromethane/EtOAc. The desired product (0.548 g) was obtained as a white solid which was combined with the filtered product to yield 0.712 g (51%) total desired product. 1H-NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.20 (d, 1H), 7.77 (d, 2H), 7.27 (t, 2H), 6.94 (t, 1H), 6.28 (d, 1H), 3.91 (s, 3H). LRMS (ESI pos) m/e 202 (M+1).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting thick suspension was filtered
  3. washwashed with ethanol
  4. customcollected
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-38930fbfabbf42c9b4b17ef41694f26f
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

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