Guanidine Hydrochloride → 4'-Methyl-2-methylsulfanyl-[4,5']bipyrimidinyl-2'-ylamine

HRID 1397165ノート

反応式

HRID 1397165 の反応式
CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)[C:5](=O)[CH3:6].C([O-])([O-])=O.[K+].[K+].Cl.[NH2:24][C:25]([NH2:27])=[NH:26]>CN(C=O)C>[CH3:6][C:5]1[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)=[CH:3][N:24]=[C:25]([NH2:27])[N:26]=1

参加物

5

反応物 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 679835344-Dimethylamino-3-(2-methylsulfanyl-pyrimidin-4-yl)-but-3-en-2-one

生成物 1

HCID 679838664'-Methyl-2-methylsulfanyl-[4,5']bipyrimidinyl-2'-ylamine収率 80%

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 4-Dimethylamino-3-(2-methylsulfanyl-pyrimidin-4-yl)-but-3-en-2-one (18) (1.02 g, 4.30 mmol) in DMF (14 mL) was added K2CO3 (1.782 g, 12.89 mmol) and Guanidine HCl (0.616 g, 6.45 mmol) and the resulting suspension was stirred at 120° C. for 1 hour. The DMF was evaporated and the crude residue partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash chromatography with a gradient of 1-12% MeOH in DCM to give the desired product as a light yellow solid (800 mg, 80%). MS (ES+): m/z=234.3/235.4 (100/20) [MH+]. HPLC: tR=1.01 minutes over 3 minutes. Purity: 70% [HPLC (LC/MS) at 220 nm].

後処理

  1. customThe DMF was evaporated
  2. customthe crude residue partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography with a gradient of 1-12% MeOH in DCM

出典と根拠

ORDレコード
ord-025e070e01ca447cbb1ff1508aaefbdb
出典データセット
uspto-grants-2014_12
特許番号
US08901147B2

反応ノート

読み込み中…