Morpholine → 5-Chloro-2-methyl-7-morpholin-4-yl-thiazolo[4,5-d]pyrimidine

HRID 1919359Notes

Reaction equation

HRID 1919359 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][C:9]([CH3:11])=[N:8][C:6]=2[N:7]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CO.CCOC(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH3:11])=[N:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 582349525,7-Dichloro-2-methylthiazolo[4,5-d]pyrimidine

Product 1

HCID 582349545-Chloro-2-methyl-7-morpholin-4-yl-thiazolo[4,5-d]pyrimidineYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5,7-dichloro-2-methyl-thiazolo[4,5-d]pyrimidine (92 mg, 0.42 mmol) in MeOH (3 mL) was added morpholine (81 μL, 0.93 mmol) and the mixture stirred at RT for 1 h. The reaction mixture was diluted with EtOAc and H2O. The organic layer was isolated, washed with brine, then dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a cream solid (102 mg, 90%).

Workup

  1. customThe organic layer was isolated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-eaea9edf5a8c483c9cb144b3e1addc39
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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