N,N-Dimethylaniline → 7-Chloro-2-(difluoromethyl)-[1,3]thiazolo[5,4-d]pyrimidine

HRID 930440ノート

反応式

HRID 930440 の反応式
[F:1][CH:2]([F:13])[C:3]1[S:4][C:5]2[N:6]=[CH:7][N:8]=[C:9](O)[C:10]=2[N:11]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[Cl:25][C:9]1[C:10]2[N:11]=[C:3]([CH:2]([F:13])[F:1])[S:4][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178518072HCID 178518072、化合物

生成物 1

HCID 867322777-Chloro-2-(difluoromethyl)-[1,3]thiazolo[5,4-d]pyrimidine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-(difluoromethyl)thiazolo[5,4-d]pyrimidin-7-ol, N,N-dimethylaniline (0.800 mL, 6.31 mmol) and phosphorus oxychloride (6.00 mL, 65.5 mmol) in toluene (20 mL) was heated at 80° C. for 6 h. The reaction mixture was cooled of rt and the solvent removed invacuo. The residue was dissolved in DCM, evaporated onto silica gel and purified by flash chromatography (Isco (80 gram)) eluting with (EtOAc):hexanes (0:1→1:3) to give an off-white crystalline solid (252 mg, 18% over 2 steps). MS m/z=221.9, 223.9 [M+H]+. Calculated for C6H2F2N3S: 221.

後処理

  1. temperatureThe reaction mixture was cooled of rt
  2. customthe solvent removed invacuo
  3. dissolutionThe residue was dissolved in DCM
  4. customevaporated onto silica gel
  5. custompurified by flash chromatography (Isco (80 gram))
  6. washeluting with (EtOAc)
  7. customhexanes (0:1→1:3) to give an off-white crystalline solid (252 mg, 18% over 2 steps)

出典と根拠

ORDレコード
ord-e75fe65d87614407ae8c605a5d82d42e
出典データセット
uspto-grants-2016_03
特許番号
US09296734B2

反応ノート

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