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

HRID 1397141노트

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HRID 1397141 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c5929c955a3e459892d2b3fa541692e8
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901147B2

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