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2-Chloro-4-(N-(2-phenylethyl)anilino)pyrimidine → 2-{4-[3-(N,N-Dimethyl)amino-2-hydroxypropoxy]anilino}-4-(N-(2-phenylethyl)anilino)pyrimidine

HRID 347751
ノート
印刷プレビュー

反応式

HRID 347751 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:24][N:25]([CH2:27][CH:28]([OH:38])[CH2:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)[CH3:26]>CN1C(=O)CCC1>[CH3:26][N:25]([CH2:27][CH:28]([OH:38])[CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([NH:35][C:2]2[N:7]=[C:6]([N:8]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:36][CH:37]=1)[CH3:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 210837402-Chloro-4-(N-(2-phenylethyl)anilino)pyrimidineHCID 227319204-[2-hydroxy-3-(N,N-dimethylamino)propoxy]aniline hydrochloride

生成物 1

HCID 210837282-{4-[3-(N,N-Dimethyl)amino-2-hydroxypropoxy]anilino}-4-(N-(2-phenylethyl)anilino)pyrimidine収率 36%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

2-Chloro-4-(N-(2-phenylethyl)anilino)pyrimidine (Reference Example E-3; 270 mg, 0.87 mmol) was dissolved in NMP (2 ml), 4-[3-(N,N-dimethyl)amino-2-hydroxypropoxy]aniline hydrochloride (Reference Example D-1; 222 mg, 0.90 mmol) was added and the mixture heated at 120° C. for 12 hours. The solvent was evaporated, the residue was resolubilized in methanol/ammonia 6M and evaporated again to dryness. The resulting solid was purified by flash chromatography using increasingly polar solvent mixtures starting with DCM and ending with DCM/methanol with 10% ammonia (87.5/12.5). Evaporation of the solvent gave a foam which was triturated in ether to give the title product as a white solid (150 mg, 36%). NMR: (400 MHz, 353K) 2.30 (s, 6H), 2.50 (m, 2H), 2.90 (m, 2H), 3.80 (m, 1H), 3.85 (m, 1H), 3.95 (br s, 1H), 4.10 (m, 2H), 5.00 (br s, 1H), 5.50 (d, 1H), 6.70 (d, 2H), 7.15 (m, 3H), 7.25(m, 4H), 7.35 (t, 1H), 7.50 (t, 2H), 7.60 (d, 2H), 7.80 (d, 1H), 8.85 (s, 1H), M.S.: (ES+) 484 (MH+).

後処理

  1. customThe solvent was evaporated
  2. customevaporated again to dryness
  3. customThe resulting solid was purified by flash chromatography
  4. temperatureusing increasingly polar solvent mixtures
  5. customEvaporation of the solvent
  6. customgave a foam which
  7. customwas triturated in ether

出典と根拠

ORDレコード
ord-c3eeb2002ddf48d3b852e626ee2eed59
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176212B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート