Water → HCID 69222016, compound

HRID 272627Notes

Reaction equation

HRID 272627 reaction equation
[CH3:1][S:2]([C:5]1[N:6]=[C:7](S(C)(=O)=O)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][O:11][C:9]=2[N:10]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[NH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1.O>CC(O)C>[CH3:1][S:2]([C:5]1[N:6]=[C:7]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][O:11][C:9]=2[N:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 69223068HCID 69223068, compound

Product 1

HCID 69222016HCID 69222016, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,4-bis-methylsulfonyl-5-phenyl-furo[2,3-d]pyrimidine (54 mg, 0.153 mmol), triethylamine (17 mg, 0.168 mmol) and 2-(aminomethyl)pyridine (18 mg, 0.168 mmol) in propan-2-ol (5 ml) was warmed to obtain a solution and stirred at ambient temperature for 2.5 hr. Water (50 ml) was then added and the mixture was extracted with dichloromethane (3×30 ml). The combined extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude (2-methanesulfonyl-5-phenyl-furo[2,3d]pyrimidin-4-yl)-pyridin-2-ylmethylamine which was purified by flash chromatography (silica) eluting with 40′-60° C. petroleum ether followed by ethyl acetate to give a white solid (17 mg), m.pt. 171-173° C.

Workup

  1. temperaturewas warmed
  2. customto obtain a solution
  3. extractionthe mixture was extracted with dichloromethane (3×30 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give the crude (2-methanesulfonyl-5-phenyl-furo[2,3d]pyrimidin-4-yl)-pyridin-2-ylmethylamine which
  7. customwas purified by flash chromatography (silica)
  8. washeluting with 40′-60° C. petroleum ether

Sources & evidence

ORD record
ord-68fb8d0a6639496fa1390645947869ff
Source dataset
uspto-grants-2008_11
Patent number
US07456187B2

Reaction notes

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