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

HRID 1692782Notes

Reaction equation

HRID 1692782 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bb80011775b74f64b34715223ffa897d
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

Loading…