Citric Acid → 1-Benzyloxypropanesulfamic acid [6-chloro-5-(4-bromophenyl)-pyrimidin-4-yl]-amide

HRID 251887Notes

Reaction equation

HRID 251887 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[K].C(O[CH2:25][CH2:26][CH2:27][NH:28][S:29]([NH2:32])(=[O:31])=[O:30])C1C=CC=CC=1.[C:33](O)(=O)[CH2:34][C:35]([CH2:40][C:41](O)=O)([C:37]([OH:39])=O)O.[CH3:46]S(C)=O>>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:32][S:29](=[O:31])(=[O:30])[NH:28][CH:27]([O:39][CH2:37][C:35]2[CH:34]=[CH:33][CH:46]=[CH:41][CH:40]=2)[CH2:26][CH3:25])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 197352625-(4-Bromophenyl)-4,6-dichloropyrimidineHCID 668722093-Benzyloxypropylsulfamide potassium

Product 1

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

Procedure

A solution of 4,6-dichloro-5-(4-bromophenyl)-pyrimidine (405 mg, 1.33 mmol) and 3-benzyloxypropylsulfamide potassium (752 mg, 2.66 mmol) in DMSO is stirred at rt under argon for 18 h. The clear solution is poured onto 10% aq. citric acid solution (50 mL) and extracted twice with EA (2×75 mL). The organic extracts are washed with water (50 mL) and the solvent is evaporated. The residue is purified by column chromatography on silica gel eluting with hexane/EA 3:2 to afford 1-benzyloxypropanesulfamic acid [6-chloro-5-(4-bromophenyl)-pyrimidin-4-yl]-amide (524 mg) as a colourless foam. LC-MS: tR=1.05 min, [M+H]+=510.96; 1H NMR (CDCl3): δ 8.44 (s, 1H), 7.71-7.65 (m, 2H), 7.40-7.28 (m, 5H), 7.18-7.12 (m, 2H), 6.90 (s, 1H), 6.05 (t, J=5.9 Hz, 1H), 4.49 (s, 2H), 3.57 (t, J 0 5.9 Hz, 2H), 3.18 (q, J=5.9 Hz, 2H), 1.88 (p, J=5.9 Hz, 2H).

Workup

  1. extractionextracted twice with EA (2×75 mL)
  2. washThe organic extracts are washed with water (50 mL)
  3. customthe solvent is evaporated
  4. customThe residue is purified by column chromatography on silica gel eluting with hexane/EA 3:2

Sources & evidence

ORD record
ord-7cf05e46ceb5418d8fde032d4099c990
Source dataset
uspto-grants-2011_01
Patent number
US07868012B2

Reaction notes

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