Triethylamine → 2-[(3-chloro-1-benzothiophen-2-yl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 576937노트

반응식

HRID 576937 반응식
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.Br[CH2:18][C:19]1[S:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[C:23]=1[Cl:24]>C(O)C>[Cl:24][C:23]1[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[S:20][C:19]=1[CH2:18][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 8167082-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 178429541HCID 178429541, 화합물

생성물 1

HCID 1784295302-[(3-chloro-1-benzothiophen-2-yl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one수율 60.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

6-methyl-2-sulfanylpyrimidin-4-ol (148 mg, 1.0 mmol) was dissolved in absolute ethanol (8 mL), then triethylamine (180 μL, 1.3 mmol) and 2-(bromomethyl)-3-chloro-1-benzothiophene (300 mg, 1.2 mmol) were added. The mixture was stirred overnight at room temperature. The precipitate was filtered, washed with ethanol and water and then diethyl ether, and dried in vacuo to afford to 2-{[(3-chloro-1-benzothiophen-2-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (195 mg, 58% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.27 (s, 3H), 4.72 (s, 2H), 5.69 (s, 1H), 6.07 (bs, 1H), 7.43-7.53 (m, 2H), 7.73-7.76 (m, 1H), 7.97-8.00 (m, 114), 12.29 (bs, 1H); LRMS (ES+) m/z 323 (100%, M+1), 325 (35%, M+3).

후처리

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol and water
  3. dry with materialdiethyl ether, and dried in vacuo

출처 및 근거

ORD 기록
ord-88a484b6ba174255a29375ac2cf69202
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040538B2

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