Water → HCID 62481580, compound

HRID 1855442Notes

Reaction equation

HRID 1855442 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]1.C(N(CC)CC)C.O>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([N:10]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 794712,4-Dichloro-6-methylpyrimidineHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 62481580HCID 62481580, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,4-dichloro-6-methylpyrimidine (579 mg, 3.55 mmol), thiomorpholine-1,1-dioxide (480 mg, 3.55 mmol) and triethylamine (0.99 mL, 7.10 mmol) in 7 mL isopropanol was refluxed overnight. Water was added and the mixture of the regioisomers were extracted with ethyl acetate. Chromatography on on Si—NH2 gel (Isolute) using cyclo-hexane/ethyl acetate(gradient 30 to 60% ethyl acetate) gave the title compound as a colourless solid (364 mg, 39%). MS ISP (m/e): 201.2 (33) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=6.39 (s, 1H), 4.20 (t broad, 4H), 3.08 (t broad, 4H), 2.41 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. additionthe mixture of the regioisomers
  3. extractionwere extracted with ethyl acetate

Sources & evidence

ORD record
ord-f934380f00cf4d9899bae18d568d8288
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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