Morpholine → 9-(2,6-dimethylstyryl)-N-(4-(dimethylphosphoryl)phenyl)-2-morpholino-9H-purin-6-amine

HRID 2041925Notes

Reaction equation

HRID 2041925 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]=[CH2:12])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([P:20]([CH3:23])([CH3:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCN([CH:36]([CH3:38])[CH3:37])C(C)C.[CH3:39][CH2:40][CH2:41][CH2:42]O.[CH3:44]S(C)=O>>[CH3:39][C:40]1[CH:41]=[CH:42][CH:38]=[C:36]([CH3:37])[C:44]=1/[CH:12]=[CH:11]/[N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:3][C:4]=2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([P:20]([CH3:23])([CH3:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 20476217n-BuOH DMSOHCID 866312602-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine

Product 1

HCID 445618289-(2,6-dimethylstyryl)-N-(4-(dimethylphosphoryl)phenyl)-2-morpholino-9H-purin-6-amine

Conditions

Temperature
120 °C

Procedure

2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine (0.05 g, 0.11 mmol) was dissolved in n-BuOH/DMSO (1.0 mL/0.2 mL) in a CEM 10 mL microwave tube and was added morpholine (95 □L, 1.1 mmol) and DIEA (96 □L, 0.55 mmol). The reaction was heated with microwave (120° C., 10 min). Solvent was removed on a rotavapor and the residue was partitioned between EtOAc/water, organic layer was separated and dried Na2SO4. The product was purified on ISCO combiFlash (12 g silica gel column, 5% MeOH/DCM) to yield the desired compound: MS [M+H]+ 559.

Workup

  1. customSolvent was removed on a rotavapor
  2. customthe residue was partitioned between EtOAc/water, organic layer
  3. customwas separated
  4. customThe product was purified on ISCO combiFlash (12 g silica gel column, 5% MeOH/DCM)

Sources & evidence

ORD record
ord-15c91aea4d05469e937ff1ea35842852
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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