Acetonitrile → 2-{4-Methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-ylamino}-ethanol

HRID 132537

反応式

HRID 132537 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.I[CH:25]([OH:27])[CH3:26].C(N=C1CCN(C)P(N(CC)CC)N1C)(C)(C)C.CC#N>CN(C=O)C.C(O)(C(F)(F)F)=O>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][CH2:26][CH2:25][OH:27])[S:3][C:4]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[N:9]=1

参加物

7

反応物 4

HCID 6342Acetonitrile2 回HCID 4479614-(2-Amino-4-methyl-5-thiazolyl)-N-(3-nitrophenyl)-2-pyrimidinamineHCID 17859945HCID 17859945、化合物HCID 69196119Tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3-diazaphosphorine

生成物 1

HCID 101098092-{4-Methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-ylamino}-ethanol

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒2 回

反応条件

温度
124 °C

実験手順

To a mixture of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine (0.33 g, 1.0 mmol) and iodoethanol (0.44 g, 2.6 mmol) in dry DMF (2 mL) was added tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3-diazaphosphorine (0.5 mL). The reaction mixture was heated at 124° C. for 20 h. The product was isolated as a brown solid by preparative RP-HPLC (Vydac 218TP1022, 9 mL/min) using a gradient from 10-70% MeCN in 0.1% aq CF3COOH over 40 min. Anal. RP-HPLC: tR=14.30 min (Vydac 218TP54, 0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, 25° C., purity>97%). 1H-NMR (CD3OD) δ: 3.30 (s, 3H, CH3), 3.91 (t, 2H, J=4.6 Hz, CH2), 4.25 (t, 2H, J=4.6 Hz, CH2), 7.21 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.54 (m, 1H, Ph-H), 7.89 (m, 2H, Ph-H), 8.59 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.90 (s, 1H, Ph-H).

後処理

  1. customThe product was isolated as a brown solid by preparative RP-HPLC (Vydac 218TP1022, 9 mL/min)
  2. customover 40 min

出典と根拠

ORDレコード
ord-ac781ecbc0c6464cbbe51fd45ef396dc
出典データセット
uspto-grants-2008_06
特許番号
US07388015B2

関連ノート

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