Potassium Carbonate → HCID 178437618、化合物

HRID 630190ノート

反応式

HRID 630190 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[C:19]([CH2:25][CH3:26])=[N:20][CH:21]=[CH:22][C:23]=1[Cl:24]>CN(C=O)C>[Cl:24][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:25][CH3:26])[C:18]=1[CH2:17][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 595895013-(Bromomethyl)-4-chloro-2-ethylpyridineHCID 178429541HCID 178429541、化合物

生成物 1

HCID 178437618HCID 178437618、化合物収率 13%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

6-methyl-2-sulfanylpyrimidin-4-ol (382 mg, 2.7 mmol) was dissolved in anhydrous DMF (15 mL), and then potassium carbonate (1.12 g, 8.1 mmol) and 3-(bromomethyl)-4-chloro-2-ethylpyridine (3.5 mmol) in DMF (10 mL) were added. The mixture was stirred for 2.5 hours at room temperature. The solid was removed by filtration and washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 5-10% DCM/MeOH to afford 2-{[(4-chloro-2-ethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (100 mg, 13% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 1.22 (t, J=7.4 Hz, 3H), 2.24 (s, 3H), 2.97 (q, J=7.4 Hz, 2H), 4.62 (s, 2H), 6.07 (bs, 1H), 7.44 (d, J=5.3 Hz, 1H), 8.40 (d, J=5.3 Hz, 1H).

後処理

  1. customThe solid was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 5-10% DCM/MeOH

出典と根拠

ORDレコード
ord-80b7e5cbca974878b9014d1671f78a6d
出典データセット
uspto-grants-2016_04
特許番号
US09315521B2

反応ノート

読み込み中…