Cesium carbonate → 6-[4-[2-(Dimethylamino)ethoxy]phenyl]-5-phenyl-N-[[(2S)-tetrahydro-2-furanyl]methyl]furo[2,3-d]pyrimidin-4-amine

HRID 502656Notes

Reaction equation

HRID 502656 reaction equation
[C:1]1([C:7]2[C:15]3[C:14]([NH:16][CH2:17][C@@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)=[N:13][CH:12]=[N:11][C:10]=3[O:9][C:8]=2[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl.[CH3:37][N:38]([CH2:40][CH2:41]Cl)[CH3:39]>CN(C=O)C>[CH3:37][N:38]([CH3:39])[CH2:40][CH2:41][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:8]2[O:9][C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH:16][CH2:17][C@@H:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[C:15]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 68463931HCID 68463931, compound

Product 1

HCID 444383186-[4-[2-(Dimethylamino)ethoxy]phenyl]-5-phenyl-N-[[(2S)-tetrahydro-2-furanyl]methyl]furo[2,3-d]pyrimidin-4-amineYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 80 (80 mg, 0.21 mmol), Cs2CO3 (0.12 g, 0.36 mmol) and N,N-dimethylaminoethyl chloride hydrochloride (59.4 mg, 0.41 mmol) in DMF (2 mL) was heated to 80° C. overnight. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography, to give 81 (27 mg, >95% e.e.). MS: 459.3 (M+1). 1HNMR (DMSO-d6) ppm 8.32 (s, 1H), 7.61-7.52 (m, 5H), 7.36 (d, 2H, J=9.00 Hz), 6.93 (d, 2H, J=9.00 Hz), 5.06 (t, 1H, J=5.50 Hz), 4.05 (t, 2H, J=6.00 Hz), 3.87-3.85 (m, 1H), 3.54-3.47 (m, 4H), 2.61 (t, 2H, J=5.50 Hz), 2.21 (s, 6H), 1.82-1.65 (m, 3H), 1.39-1.25 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-219ff438da4048deae47d897a84f1a23
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

Loading…