Guanidine Hydrochloride → 4'-(Cyclopropylmethyl)-2-(methylthio)-4,5'-bipyrimidin-2'-amine

HRID 1397141ノート

反応式

HRID 1397141 の反応式
[CH:1]1([CH2:4][C:5](=O)/[C:6](/[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[CH:7]\N(C)C)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:27][C:28]([NH2:30])=[NH:29]>CN(C=O)C>[CH:1]1([CH2:4][C:5]2[C:6]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:7][N:27]=[C:28]([NH2:30])[N:29]=2)[CH2:2][CH2:3]1

参加物

5

反応物 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 67983763(3Z)-1-Cyclopropyl-4-(dimethylamino)-3-[2-(methylsulfanyl)pyrimidin-4-yl]but-3-en-2-one

生成物 1

HCID 679837974'-(Cyclopropylmethyl)-2-(methylthio)-4,5'-bipyrimidin-2'-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of (Z)-1-cyclopropyl-4-(dimethylamino)-3-(2-(methylthio)pyrimidin-4-yl)but-3-en-2-one (3) (2.07 g, 7.46 mmol) in DMF (62.2 ml) was added potassium carbonate (3.09 g, 22.39 mmol) and guanidine hydrochloride (1.065 g, 11.19 mmol). The resulting suspension was stirred at 120° C. After 45 minutes, the reaction was complete. The reaction mixture was concentrated in vacuo, then was taken up in EtOAc. The organic solution was washed with water, followed by brine, dried over sodium sulfate, then concentrated in vacuo. The crude residue was dried over high vacuum for 18 h to obtain the desired product as a bright orange product (2.17 g, quant. yield). MS (ES+): m/z=250.1 (50) [MH+]. HPLC: tR=1.13 min over 3 min. Purity: 100% [HPLC (LC/MS) at 220 nm]. 1H NMR (400 MHz, DMSO-d6) d ppm 0.06-0.13 (m, 2H) 0.33-0.41 (m, 2 H) 0.96-1.11 (m, 1 H) 2.52-2.57 (m, 3 H) 2.79 (d, J=7.07 Hz, 2 H) 7.03 (s, 2 H) 7.39 (d, J=5.56 Hz, 1 H) 8.44 (s, 1 H) 8.60 (d, J=5.56 Hz, 1 H).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe organic solution was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dry with materialThe crude residue was dried over high vacuum for 18 h

出典と根拠

ORDレコード
ord-c5929c955a3e459892d2b3fa541692e8
出典データセット
uspto-grants-2014_12
特許番号
US08901147B2

反応ノート

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