Acetone → 2-(5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol

HRID 1365782노트

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HRID 1365782 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+].[CH3:25][C:26]([CH3:28])=[O:27].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]([C:26]([OH:27])([CH3:28])[CH3:25])[S:8][C:6]=2[N:7]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 2724682Lithium diisopropylamideHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine

생성물 1

HCID 576854202-(5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 22742125Tetrahydrofuran heptane ethylbenzol용매

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온도
-78 °C

실험 절차

4-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine 14 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. Acetone (6 eq) was added and the solution was stirred at −78° C. for an additional one hour. Ice 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. The resulting residue was purified on silica gel to give the light yellow solid of 2-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol 68.

후처리

  1. stirringthe solution was stirred at −78° C. for an additional one hour
  2. additionIce was added
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified on silica gel

출처 및 근거

ORD 기록
ord-c8e6be6f7d9046dab2b7d67bdee17cd4
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893059B2

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