Ethanethiol → 3-hydroxy-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one

HRID 625954노트

반응식

HRID 625954 반응식
C([O:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:14]=1)C1C=CC=CC=1.C(S)C.B(F)(F)F.CCOCC>CO>[OH:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([C:15]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][N:16]=2)[CH:14]=1

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 674194493-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one

생성물 1

HCID 533799013-hydroxy-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one수율 46%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one (21 mg, 0.057 mmol) was added ethanethiol (31.8 mg, 0.512 mmol) followed by BF3.OEt2 (73 mg, 0.512 mmol). The resulting solution was stirred at room temperature for 18 h, diluted with MeOH and concentrated. Purification by preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 7.3 mg 3-hydroxy-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one (46%) as a light purple solid. 1H NMR (500 MHz, DMSO-d6): δ 9.41 (br s, 1H), 8.84 (d, J=5.3 Hz, 1H); 8.44 (s, 1H); 8.33 (s, 2 H); 7.90 (d, J=5.3 Hz, 1H); 7.72 (s, 1H); 7.59 (s, 3H); 3.65 (s, 3H). High resolution mass spec (FT/ICR) calc (M+H)+=280.1081 found 280.1080.

후처리

  1. concentrationconcentrated
  2. customPurification
  3. additionby preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA)

출처 및 근거

ORD 기록
ord-44cc42d15a9b4df9b82838e8a8b4b5b2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309199B2

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