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

HRID 625954ノート

反応式

HRID 625954 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-44cc42d15a9b4df9b82838e8a8b4b5b2
出典データセット
uspto-grants-2016_04
特許番号
US09309199B2

反応ノート

読み込み中…