Sodium Hydroxide → HCID 69217957, compound

HRID 900161Notes

Reaction equation

HRID 900161 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].Cl[CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([NH:15][CH2:37][CH2:38][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 767274-(2-Chloroethyl)morpholineHCID 69217072HCID 69217072, compound

Product 1

HCID 69217957HCID 69217957, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 7-(2,4-dimethoxybenzyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (43.7 mg, 0.1 mmol) and sodium hydroxide powder (20 mg, 0.50 mmol) in DMF (1 mL) was added N-(2-chloroethyl)morpholine (30 mg, 0.2 mmol). The mixture was stirred for 5 minutes at 150° C. under microwave irradiation (using powerMAX™). The reaction mixture was then cooled and diluted with EtOAc (25 mL). The mixture was extracted twice with water (10 mL) and then brine. The organic layer was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel to give the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionThe mixture was extracted twice with water (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f12c4bbc94a84653a8a9e9e179b32870
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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