Triethylamine → HCID 15346377, compound

HRID 1450004Notes

Reaction equation

HRID 1450004 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[NH2:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([O:17][CH3:18])[N:10]=1.[CH:19]1([C:22]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[NH2:31])=[O:23])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH:19]1([C:22]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[NH:31][S:2]([NH:5][C:6]([NH:8][C:9]2[N:10]=[C:11]([O:17][CH3:18])[CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)=[O:7])(=[O:4])=[O:3])=[O:23])[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 15346026HCID 15346026, compound

Product 1

HCID 15346377HCID 15346377, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Chlorosulfonyl isocyanate (2.0 mL, 3.25 g, 23.0 mmol) is added to a solution of 2-amino-4,6-dimethoxypyrimidine (4.13 g, 26.6 mmol) in methylene chloride at 0° C. The resulting mixture is stirred for 30 minutes and a solution of 2-amino-5-fluorophenyl cyclopropyl ketone (4.77 g, 26.6 mmol) and triethylamine (6.3 mL, 4.57 g, 45.2 mmol) in methylene chloride is slowly added to the mixture. The resulting solution is stirred at room temperature for 18 hours, concentrated in vacuo and dissolved in methanol. The methanol solution is adjusted to about pH 1 with 10% hydrochloric acid and extracted with methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and 30% to 50% ethyl acetate in hexanes solutions affords a residue which is crystallized from an ether/petroleum ether solution to give the title product as a pale yellow solid (2.83 g, 24%, mp 76°-78° C.).

Workup

  1. stirringThe resulting solution is stirred at room temperature for 18 hours
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in methanol
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue
  8. customaffords a residue which
  9. customis crystallized from an ether/petroleum ether solution

Sources & evidence

ORD record
ord-428e44f8375648269207f5d51d0d4170
Source dataset
uspto-grants-1997_02
Patent number
US05599996

Reaction notes

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