Diisopropylethylamine → 4-[(1,3-Dithiolan-2-yl)-methyl]amino-5,6-diphenyl furo[2,3-d]pyrimidine

HRID 502657Notes

Reaction equation

HRID 502657 reaction equation
Br[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[S:23]1[CH2:27][CH2:26][S:25][CH:24]1NC.C[CH2:31][N:32](C(C)C)C(C)C>C(O)CCC>[S:25]1[CH2:26][CH2:27][S:23][CH:24]1[CH2:31][NH:32][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 586033114-Bromo-5,6-diphenyl-furo[2,3-d]pyrimidineHCID 866032271,3-Dithiolan-2-yl-methylamine

Product 1

HCID 860887714-[(1,3-Dithiolan-2-yl)-methyl]amino-5,6-diphenyl furo[2,3-d]pyrimidineYield 34.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 69 (150 mg, 0.86 mmol), 1,3-dithiolan-2-yl-methylamine (240 μL, 1.78 mmol), and DIEA 0.31 mL (1.78 mmol) in 1-butanol (1 mL) was heated to 120° C. for 2 h. After cooling, the reaction mixture was concentrated, and the residue was purified by silica gel column chromatography, affording 110 (121 mg). LCMS and 1HNMR are identical with the product obtained from method 1.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dcf7bbea9429499eb6e26c15bf6ea122
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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