Cesium carbonate → HCID 58292559, compound

HRID 1798210Notes

Reaction equation

HRID 1798210 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.[NH2:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.CCOC(C)=O>[NH2:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)[CH:25]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2380124-Amino-6-chloropyrimidineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292559HCID 58292559, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To the mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.04 g, 4 mmol) and 4-amino-6-chloropyrimidine (520 mg, 4 mmol) in CH3CN (20 ml), added Cs2CO3 (3.9 g, 12 mmol). The mixture was stirred at 50° C. for 24 hours. The result mixture was diluted with EtOAc (200 ml), washed with water and brine, dried over Na2SO4. Concentrated to give light yellow oil used for next step without further purification. MS (ESI negative): (M−H)−=342.1.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationConcentrated
  4. customto give light yellow oil
  5. customused for next step without further purification

Sources & evidence

ORD record
ord-499fd6c9c4dd479781c9158b10f0e5f7
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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