Dimethylformamide → 5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

HRID 1365806

反応式

HRID 1365806 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:27]=[O:28].C(Cl)Cl>O1CCCC1.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[N:10]=[C:9]([CH:27]=[O:28])[S:8][C:6]=2[N:7]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 2724682Lithium diisopropylamideHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine

生成物 1

HCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 22742125Tetrahydrofuran heptane ethylbenzol溶媒

反応条件

温度
-78 °C

実験手順

5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine was slurried in tetrahydrofuran and cooled to −78° C. under nitrogen. Two equivalents of 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene was added slowly and the solution was stirred for 30 minutes. dimethylformamide (6 eq) was added and the solution was stirred at −78° C. for an additional one hour. The solution was warmed to 0° C. and ice cold 0.1N hydrochloric acid was added and the solution was warmed to room temperature before extraction with methylene chloride. The organic layer was dried with sodium sulfate and concentrated to give 5-chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde.

後処理

  1. stirringthe solution was stirred at −78° C. for an additional one hour
  2. temperatureThe solution was warmed to 0° C.
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-ada90689861e4a13a80e6bb74acd5f57
出典データセット
uspto-grants-2011_02
特許番号
US07893059B2

関連ノート

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