Morpholine → 4-(2-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine

HRID 334113Notes

Reaction equation

HRID 334113 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]([CH3:11])[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)C.C(OCC)(=O)C>[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[N:10]([CH3:11])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 147277632,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidine

Product 1

HCID 735546554-(2-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholineYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

A mixture of 2,4-dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (1.25 g, 6.19 mmol), morpholine (1.08 mL, 12.37 mmol), and N,N-diisopropylethylamine (2.37 mL, 13.61 mmol) in N,N-dimethylformamide (36 mL) was stirred at RT under N2 for 15 h. The reaction mixture was diluted with 1:1 diethyl ether/ethyl acetate, and the organic layer was washed with 1:1 water/brine (3×) and brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 1.47 g (94.0%) of 4-(2-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)morpholine as a white solid. MS(ESI) m/z: 253.1/255.1 [M+1]−.

Workup

  1. washthe organic layer was washed with 1:1 water/brine (3×) and brine (1×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9905e18005494e4e8a9e681347c1961b
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

Loading…