Water → (3R,5S)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-5-hydroxymethyl-pyrrolidin-3-ol

HRID 70097

反応式

HRID 70097 の反応式
Cl[C:2]1[C:3]2[S:23](=[O:24])[CH2:22][CH2:21][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.FC(F)(F)C(O)=O.[OH:32][CH2:33][C@H:34]1[NH:38][CH2:37][C@H:36]([OH:39])[CH2:35]1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1.ClCCl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]3[N:7]=[C:2]([N:38]4[C@H:34]([CH2:33][OH:32])[CH2:35][C@@H:36]([OH:39])[CH2:37]4)[C:3]4[S:23](=[O:24])[CH2:22][CH2:21][C:4]=4[N:5]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 594758954-Chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxideHCID 66735651(3R,5S)-5-hydroxymethyl-pyrrolidin-3-ol trifluoroacetate

生成物 1

HCID 59708409(3R,5S)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-5-hydroxymethyl-pyrrolidin-3-ol収率 75.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

220 mg (0.57 mmol) 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide, 159.23 mg (0.69 mmol) (3R,5S)-5-hydroxymethyl-pyrrolidin-3-ol trifluoroacetate (prepared from commercial Boc-trans-4-hydroxy-L-prolinol) and 197.52 μl (1.15 mmol) diisopropylethylamine are placed in 4 ml dioxane, and heated to 120° C. in the microwave for 0.3 hours. Then the reaction mixture is combined with water and dichloromethane and extracted. The organic phase is separated off using a phase separation cartridge and evaporated to dryness. 200.3 mg of the product (75%) are obtained as a racemic mixture. Analytical HPLC-MS (method A): RT=2.26 min.

後処理

  1. extractionextracted
  2. customThe organic phase is separated off
  3. customa phase separation cartridge
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-ec8bf9e1cbfe48b789032d5231959db7
出典データセット
uspto-grants-2014_09
特許番号
US08822474B2

関連ノート

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