Diethyl Ether → HCID 178437123, 화합물

HRID 630151노트

반응식

HRID 630151 반응식
Br[CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][N:6]=[CH:5][C:4]=1[CH2:11][CH3:12].[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C.CCOCC>C(O)C>[CH2:11]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH2:9][CH3:10])[C:3]=1[CH2:2][S:20][C:18]1[N:17]=[C:16]([OH:21])[CH:15]=[C:14]([CH3:13])[N:19]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 595893084-(Bromomethyl)-3,5-diethylpyridineHCID 178429541HCID 178429541, 화합물

생성물 1

HCID 178437123HCID 178437123, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of crude 4-(bromomethyl)-3,5-diethylpyridine (2.07 g, 9.07 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (0.838 g, 5.89 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (3.21 g, 4.42 mL 31.75 mmol), and the reaction mixture was allowed to stir at room temperature overnight. The solvent was evaporated to provide a crude residue. Ether was added to precipitate the triethylamine hydrobromide salt. The solid was filtered and washed with ether several times. The combined ether layers were evaporated, and the crude residue was purified by Combiflash using 0-10% MeOH in dichloromethane to provide 2-{[(3,5-diethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid; 1H NMR (400 MHz, DMSO-d6): δ 1.23 (t, 6H), 1.40 (t, 3H), 2.64 (q, 4H), 4.44 (q, 2H), 8.36 (s, 2H); M+1 290.4.

후처리

  1. customThe solvent was evaporated
  2. customto provide a crude residue
  3. customto precipitate the triethylamine hydrobromide salt
  4. filtrationThe solid was filtered
  5. washwashed with ether several times
  6. customThe combined ether layers were evaporated
  7. customthe crude residue was purified by Combiflash

출처 및 근거

ORD 기록
ord-345715652de54e72a8dd39c99ddcd2a0
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315521B2

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