Diisopropylethylamine → (5,6-Diphenyl-furo[2,3-d]pyrimidin-4-yl)-(tetrahydro-thiophen-2-ylmethyl)-amine

HRID 502673Notes

Reaction equation

HRID 502673 reaction equation
FC(F)(F)C([O-])=O.[S:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH3+:14].Br[C:16]1[C:17]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:23]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:22][C:18]=2[N:19]=[CH:20][N:21]=1.CCN(C(C)C)C(C)C>C(O)CCC>[C:25]1([C:24]2[C:17]3[C:16]([NH:14][CH2:13][CH:9]4[CH2:10][CH2:11][CH2:12][S:8]4)=[N:21][CH:20]=[N:19][C:18]=3[O:22][C:23]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 586033114-Bromo-5,6-diphenyl-furo[2,3-d]pyrimidineHCID 68462148(Tetrahydrothiophen-2-yl)methylammonium trifluoroacetate

Product 1

HCID 68458217(5,6-Diphenyl-furo[2,3-d]pyrimidin-4-yl)-(tetrahydro-thiophen-2-ylmethyl)-amineYield 75.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of (tetrahydrothiophen-2-yl)methylammonium trifluoroacetate 223 (60 mg, 0.25 mmol) and 4-bromo-5,6-diphenylfuro[2,3-d]pyrimidine 69 (46 mg, 0.15 mmol) was stirred in n-butanol (2 mL) and DIPEA (0.25 mL) was added. The mixture was heated at reflux for 1 hour, cooled and the solvent was evaporated. The residue was purified by flash column chromatography to afford 230 (44 mg, 73%) as a yellow oil. 1H NMR (CDCl3): 8.32 (1H, s); 7.56-7.40 (7H, m); 7.23-7.15 (3H, m); 5.00 (1H, br t, J=4 Hz); 3.69-3.60 (1H, m); 3.55-3.35 (2H, m); 2.75-2.60 (2H, m); 1.95-1.75 (3H, m) and 1.60-1.48 (1H, m).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-840df374407c43cab78e30488d85e5f9
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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