Potassium Carbonate → HCID 461300, compound

HRID 263394Notes

Reaction equation

HRID 263394 reaction equation
[OH:1][B:2]([OH:16])[CH2:3][CH2:4][CH2:5][CH2:6]N1C=C(C)C(=O)NC1=O.[NH2:17][C:18]1[N:26]=[C:25]2[C:21]([NH:22][CH:23]=[N:24]2)=[C:20]([Cl:27])[N:19]=1.BrCCCCB(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:17][C:18]1[N:26]=[C:25]2[C:21]([N:22]=[CH:23][N:24]2[CH2:6][CH2:5][CH2:4][CH2:3][B:2]([OH:16])[OH:1])=[C:20]([Cl:27])[N:19]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 461298HCID 461298, compoundHCID 53603492-Amino-6-chloropurineHCID 14316432(4-Bromobutyl)boronic acid

Product 1

HCID 461300HCID 461300, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).

Sources & evidence

ORD record
ord-0a945f79499b45f9b4a81bbacd2711e1
Source dataset
uspto-grants-1997_07
Patent number
US05643893

Reaction notes

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