Thymine → HCID 461298, compound

HRID 263392Notes

Reaction equation

HRID 263392 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:15]=[C:13]([CH3:14])[C:11](=[O:12])[NH:10][C:8]1=[O:9].Br[CH2:17][CH2:18][CH2:19][CH2:20][B:21]([OH:23])[OH:22]>CN(C)C=O>[OH:22][B:21]([OH:23])[CH2:20][CH2:19][CH2:18][CH2:17][N:7]1[CH:15]=[C:13]([CH3:14])[C:11](=[O:12])[NH:10][C:8]1=[O:9]

Participants

5

Reactant 3

HCID 1135ThymineHCID 11430Potassium CarbonateHCID 14316432(4-Bromobutyl)boronic acid

Product 1

HCID 461298HCID 461298, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%.

Workup

  1. additionwas added dropwise
  2. stirringstirring
  3. waitwas continued 2 days at room temperature
  4. filtrationAfter the potassium carbonate was filtered
  5. customthe dimethylformamide was evaporated under high vacuum
  6. customThe residue was purified on a silica gel column
  7. washeluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15)
  8. customevaporated

Sources & evidence

ORD record
ord-81601c1a2c9d49b898d2b95a1b731986
Source dataset
uspto-grants-1997_07
Patent number
US05643893

Reaction notes

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