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

HRID 1397165노트

반응식

HRID 1397165 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-025e070e01ca447cbb1ff1508aaefbdb
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901147B2

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