Potassium Carbonate → HCID 69216254, compound

HRID 900164Notes

Reaction equation

HRID 900164 reaction equation
[CH2:1]([N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:2]=[CH2:3].[S:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH2:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCOC(C)=O>[CH2:1]([N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:32][CH2:31][CH:27]3[CH2:28][CH2:29][CH2:30][S:26]3)[C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15629560Tetrahydro-2-thiophenemethanamineHCID 86603371HCID 86603371, compound

Product 1

HCID 69216254HCID 69216254, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 7-allyl-4-chloro-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine (Example 3, Step B; 200 mg, 0.58 mmol) and 140 mg of (tetrahydrothiophen-2-yl)methylamine (1.20 mmol) in N,N-dimethylformamide (3 mL) was added potassium carbonate (200 mg, 1.45 mmol). The mixture was stirred for 5 minutes at 120° 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 preparative HPLC (C8 column, water, acetonitrile, 0.1% TFA) 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 preparative HPLC (C8 column, water, acetonitrile, 0.1% TFA)

Sources & evidence

ORD record
ord-14162b92b5d14577acf92fd1eee2df90
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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