Acetylacetone → 4-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

HRID 230273

반응식

HRID 230273 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[CH3:25][C:26](=O)[CH2:27][C:28](=[O:30])[CH3:29]>C1COCC1>[C:28]([C:27]1[CH:21]([C:20]2[CH:23]=[CH:24][C:17]([C:15]#[N:16])=[CH:18][CH:19]=2)[NH:12][C:10](=[S:11])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[C:26]=1[CH3:25])(=[O:30])[CH3:29]

참가 물질

5

반응물 3

HCID 31261AcetylacetoneHCID 660424-CyanobenzaldehydeHCID 7358443-(Trifluoromethyl)phenylthiourea

생성물 1

HCID 115968194-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-Trifluoromethylphenyl thiourea (200 mg, 0.91 mol), 4-cyanobenzaldehyde (238.2 mg, 1.82 mmol) and 2,4-pentanedione (181.9 mg, 1.82 mmol) are dissolved in 5 ml THF. Ethyl polyphosphate (0.30 g) is added and the reaction mixture is stirred at reflux temperature overnight. After cooling to room temperature, the reaction is quenched with 10 ml of water and extracted with 10 ml ethyl acetate (2×). The combined organic layers are dried with sodium sulfate and the solvent is removed in vacuo. The product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10).

후처리

  1. temperatureat reflux temperature overnight
  2. customthe reaction is quenched with 10 ml of water
  3. extractionextracted with 10 ml ethyl acetate (2×)
  4. dry with materialThe combined organic layers are dried with sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

출처 및 근거

ORD 기록
ord-ba50b72af48440d5a5ddf0f361cfa40a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566723B2

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