Thiourea → HCID 86690856, compound

HRID 1465551Notes

Reaction equation

HRID 1465551 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][C:13]2[CH:18]=[N:17][C:16]([O:19][CH3:20])=[CH:15][N:14]=2)=[CH:7][C:6]=1[CH3:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[CH3:20][O:19][C:16]1[N:17]=[CH:18][C:13]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]([C:3]3[N:22]=[C:23]([NH2:25])[S:24][CH:2]=3)=[C:6]([CH3:21])[CH:7]=2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690857HCID 86690857, compound

Product 1

HCID 86690856HCID 86690856, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-{4-((5-methoxypyrazin-2-yl)oxy)-2,6-dimethylphenyl}ethanone (15-2, 2.70 g, 7.69 mmol) and thiourea (0.59 g, 7.69 mmol) in 95% EtOH (11.0 mL) was heated at reflux for 60 min. The solution was concentrated and added with water and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was purified by column chromatography on silica gel (EtOAc:hexanes=2:1 as eluant) to give 4-{4-((5-methoxypyrazin-2-yl)oxy)-2,6-dimethylphenyl}thiazol-2-amine (15-3, 0.40 g) as yellow oils in 16% yield: 1H NMR (500 MHz, CDCl3) δ 7.91 (s, 1 H), 7.87 (s, 1 H), 6.77 (s, 2 H), 6.28 (s, 1 H), 5.19 (bs, 2 H), 3.96 (s, 3 H), 2.15 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water and saturated aqueous Na2CO3 (1.0 mL)
  5. customThe resultant precipitate was purified by column chromatography on silica gel (EtOAc:hexanes=2:1 as eluant)

Sources & evidence

ORD record
ord-d52c793fad9645fe9c85c11f7892fd17
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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