Formic Acid → 2-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine

HRID 60189ノート

反応式

HRID 60189 の反応式
Cl[C:2]1[C:7]([NH:8][C:9](=O)[CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[C:6](Cl)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1.NC(N)=[S:25].[CH3:27][CH2:28][OH:29].[CH:30]([OH:32])=O>>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[CH2:10][C:9]1[S:25][C:2]2[N:3]=[C:4]([S:21][CH3:22])[N:5]=[C:30]([OH:32])[C:7]=2[N:8]=1.[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[CH2:10][C:9]1[S:25][C:2]2[N:3]=[C:4]([S:21][CH3:22])[N:5]=[C:6]([O:29][CH2:28][CH3:27])[C:7]=2[N:8]=1

参加物

6

反応物 4

HCID 284Formic AcidHCID 702EthanolHCID 2723790ThioureaHCID 57742481HCID 57742481、化合物

生成物 2

HCID 685191702-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine収率 41%HCID 178503525HCID 178503525、化合物収率 18%

反応条件

温度
90 °C

実験手順

To a mixture of N-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-2-(2,6-dichloro-phenyl)-acetamide (10 g, 25 mmol), thiourea (1.9 g, 25 mmol), and EtOH (100 mL) was added formic acid (0.8 mL) at rt. The resulting mixture was heated to 90° C. After 12 h, the reaction mixture was cooled and concentrated. The resulting residue was collected by vacuum filtration and washed with H2O (50 mL) followed by hexanes (50 mL). The title compound purified by FCC to afford 2-(2,6-dichloro-benzyl)-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-7-ol (1.6 g, 18%) and 2-(2,6-dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine (4 g, 41%) as colorless solids.

後処理

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe resulting residue was collected by vacuum filtration
  4. washwashed with H2O (50 mL)
  5. customThe title compound purified by FCC

出典と根拠

ORDレコード
ord-593e427655594fdaa06c8697a1ea3ecc
出典データセット
uspto-grants-2016_09
特許番号
US09440978B2

反応ノート

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