Dimethylformamide → HCID 66699767, compound

HRID 388096Notes

Reaction equation

HRID 388096 reaction equation
Br[C:2]1[N:3]=[C:4]2[N:10]([C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:9](=[O:19])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.BrC1N=C2N([C@@H:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH3:33])C(=O)NC2=NC=1.C(=O)([O-])[O-].[Cs+].[Cs+].COS(OC)(=O)=O.[CH3:53][N:54](C)C=O>>[CH3:20][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:39]3[CH:38]=[CH:37][CH:36]=[C:35]4[C:34]=3[CH:32]=[CH:33][CH:53]=[N:54]4)[N:3]=[C:4]2[N:10]([C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]1=[O:19]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 24815412HCID 24815412, compoundHCID 86626388HCID 86626388, compound

Product 1

HCID 66699767HCID 66699767, compoundYield 83%

Conditions

Temperature
55 °C

Procedure

(R)-5-Bromo-1-methyl-3-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. To a solution of (R)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.360 g, 1.13 mmol) in dimethylformamide (3 mL) was added cesium carbonate (excess) followed by dimethylsulfate (0.150 g, 1.13 mmol). The solution was heated to 55° C. in a screw capped tube. After one hour, the solution was filtered to remove cesium carbonate salts. The filtrate was condensed under reduced pressure and the crude product purified via Biotage silica gel chromatography (5-50% ethyl acetate/hexanes) to afford the title compound (0.306 g, 83% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.57 (d, 2H), 7.32 (m, 3H), 5.77 (q, 1H), 3.42 (s, 3H), 2.04 (d, 3H); 13C NMR (75 MHz, CHCl3) δ 52.6 (C═O); MS (ESI) m/z 333.3 [M+1]+, 335.3 [M+2]+.

Workup

  1. customcapped tube
  2. filtrationthe solution was filtered
  3. customto remove cesium carbonate salts
  4. customcondensed under reduced pressure
  5. customthe crude product purified via Biotage silica gel chromatography (5-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aff3aca20a4644f58909e0f7764dcfa9
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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