Cesium carbonate → HCID 11212907, compound

HRID 2373903Notes

Reaction equation

HRID 2373903 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:18]3[CH2:21][CH2:20][CH2:19]3)=[N:9][C:10]=2[C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1>CN(C=O)C>[C:37]([O:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][O:17][C:13]2[CH:12]=[C:11]([C:10]3[N:9]=[C:8]([CH:18]4[CH2:21][CH2:20][CH2:19]4)[N:4]4[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=34)[CH:16]=[CH:15][CH:14]=2)=[CH:35][CH:34]=1)([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11716093HCID 11716093, compoundHCID 200354261-(Bromomethyl)-4-tert-butoxybenzene

Product 1

HCID 11212907HCID 11212907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (200 mg, 0.71 mmol) in DMF (3.5 mL) was charged with Cs2CO3 (348 mg, 1.07 mmol) and stirred at rt for 30 min. A solution of 1-bromomethyl-4-tert-butoxy-benzene (162 mg, 0.71 mmole) in 0.5 mL of DMF, was added to the reaction mixture. After 15 h, the reaction was complete by LC/MS analysis. The product was an orange/brown solid. The crude product was chromatographed on silica gel [Jones Flashmaster, 5 g cartridge, eluting with 10% ethyl acetate]. The product was then recrystalized with ethyl acetate and hexanes yielding the title compound as a white solid; 1H NMR (CDCl3, 400 MHz) δ 1.36 (s, 9H), 2.11-2.23 (m, 2H), 2.45-2.52 (m, 2H), 2.59-2.69 (m, 2H), 3.77-3.85 (m, 1H), 5.08 (s, 2H), 5.49 (brs, 2H), 7.01-7.04 (m, 3H), 7.05 (dd, J=4.00 Hz, 1H), 7.10 (d, J=5.02 Hz, 1H), 7.23-7.25 (m, 1H), 7.29 (q, J=40 Hz, 1H), 7.34-7.36 (m, 2H), 7.41 (t, J=16 Hz, 1H); MS (ES+): m/z 443.04 (100) [MH+].

Workup

  1. waitAfter 15 h
  2. customThe crude product was chromatographed on silica gel [Jones Flashmaster, 5 g cartridge, eluting with 10% ethyl acetate]
  3. customThe product was then recrystalized with ethyl acetate and hexanes yielding the title compound as a white solid

Sources & evidence

ORD record
ord-5d68ffb901cc407f98742c14ef8a30d9
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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