Ethylene Glycol → 1-Benzyloxypropanesulfamic acid[6-(2-hydroxyethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide

HRID 251888Notes

Reaction equation

HRID 251888 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9](=[O:23])(=[O:22])[NH:10][CH:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH3:13])[C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1.[CH2:31]([OH:34])[CH2:32][OH:33]>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[OH:33][CH2:32][CH2:31][O:34][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9](=[O:23])(=[O:22])[NH:10][CH:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH3:13])[C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 866172161-Benzyloxypropanesulfamic acid [6-chloro-5-(4-bromophenyl)-pyrimidin-4-yl]-amide

Product 1

HCID 1317286121-Benzyloxypropanesulfamic acid[6-(2-hydroxyethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Conditions

Temperature
87.5 °C

Procedure

To as suspension of 1-benzyloxypropanesulfamic acid[6-chloro-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (524 mg, 1.02 mmol) in ethylene glycol (10 mL) is added potassium tert. butylate (1.15 g, 10.2 mmol). The resulting clear solution is stirred at 85-90° C. for 48 h before it is cooled to rt, diluted with 10% aq. citric acid solution (75 mL) and extracted with EA (2×75 mL). The organic extracts are washed with water (2×75 mL) and the solvent is removed in vacuo. The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1 to give 1-benzyloxypropanesulfamic acid[6-(2-hydroxyethoxy)-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (517 mg) as a colourless foam. LC-MS: tR=0.97 min, [M+H]+=536.99; 1H NMR (CDCl3): δ 8.34 (s, 1H), 7.65-7.60 (m, 2H), 7.38-7.29 (m, 5H), 7.20-7.15 (m, 2H), 6.86 (s br, 1H), 5.98 (t br, J=5.9 Hz, 1H), 4.51-4.45 (m, 4H), 3.86-3.82 (m, 2H), 3.56 (t, J=5.9 Hz, 2H), 3.17 (q, J=6.4 Hz, 2H), 2.54 (s br, 1H), 1.93-1.84 (m, 2H).

Workup

  1. temperatureis cooled to rt
  2. extractionextracted with EA (2×75 mL)
  3. washThe organic extracts are washed with water (2×75 mL)
  4. customthe solvent is removed in vacuo
  5. customThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

Sources & evidence

ORD record
ord-b3958732768f4802842ab860cfff151b
Source dataset
uspto-grants-2011_01
Patent number
US07868012B2

Reaction notes

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