4-Methyloxybenzyl chloride → (+)-1,4-Dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester hydrochloride

HRID 1722411노트

반응식

HRID 1722411 반응식
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:3]=1[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][Cl:31])=[CH:28][CH:27]=1>O1CCCC1.CCOCC>[ClH:31].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][S:8][C:6]2[NH:7][C:2]([CH3:1])=[C:3]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH:4]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=3)[N:5]=2)=[CH:28][CH:27]=1

참가 물질

5

반응물 2

HCID 699934-Methyloxybenzyl chloride2회HCID 2748290Isopropyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

생성물 1

HCID 86743288(+)-1,4-Dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester hydrochloride

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

(+)-1,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-thioxo-5-pyrimidinecarboxylic acid, 1-methylethyl ester (2.6 mmol, 884 mg) was dissolved in dry tetrahydrofuran and cooled to 0° C. 4-Methoxybenzyl chloride (1.1 eq, 32.9 mmol, 393 μl) was added dropwise. After the addition was complete, the bath was removed and the reaction stirred at room temperature for two hours. The mixture was then heated at 65° C. for 16 hours. TLC 35:65:acetone:hexane showed an incomplete reaction, so additional 4-methoxybenzyl chloride (0.5 eq, 1.3 mmol, 176 μl) was added to the mixture. After seven hours at 65° C., the mixture was allowed to come to room temperature and diluted with ether. As the mixture cooled to 0° C., a white solid formed. The solid was collected by suction filtration, washed with ether, and dried to afford (+)-1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester hydrochloride, 493 mg (38%).

후처리

  1. additionAfter the addition
  2. customthe bath was removed
  3. temperatureThe mixture was then heated at 65° C. for 16 hours
  4. customan incomplete reaction
  5. waitAfter seven hours at 65° C.
  6. customto come to room temperature
  7. temperatureAs the mixture cooled to 0° C.
  8. customa white solid formed
  9. filtrationThe solid was collected by suction filtration
  10. washwashed with ether
  11. customdried

출처 및 근거

ORD 기록
ord-a7ec2371025d49fbb662b92587d4de17
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855301

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