Water → HCID 178507153, compound

HRID 32487

Reaction equation

HRID 32487 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:6][N:5]=[C:4]2[O:15][CH:16]=[CH:17][C:3]=12.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.O>C1COCC1>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:26])=[O:25])=[CH:12][CH:13]=2)[CH2:6][N:5]=[C:4]2[O:15][CH:16]=[CH:17][C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178507147HCID 178507147, compound

Product 1

HCID 178507153HCID 178507153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To compound 4-Amino-3-(4-aminophenyl)furo[2,3-d]pyrimidine (9) (24 mg, 0.044 mmol) in THF (1 mL), benzenesulfonyl chloride (6.8 uL, 0.053 mmol), and N,N-diisopropylethylamine (9 uL, 0.053 mmol) were added. After the mixture was stirred at room temperature for 6 h, water was added to quench the reaction. The solution was extracted with EtOAc. The organic layer was separated, dried (MgSO4), and filtered. The solvent was evaporated. The residue was purified by gilson to afford the desired product MS(ES) m/e 367 [M+H]+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe solution was extracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customThe residue was purified by gilson

Sources & evidence

ORD record
ord-37a5f4176ec244aab45faa66b62e8c22
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Linked notes

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