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

HRID 1365806

반응식

HRID 1365806 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 22742125Tetrahydrofuran heptane ethylbenzol용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ada90689861e4a13a80e6bb74acd5f57
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893059B2

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