Water → 2,4-Bis(methyloxy)-5-(2-methyl-1,3-thiazol-4-yl)pyrimidine

HRID 1925022Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH3:8][O:9][C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13](B(O)O)=[CH:12][N:11]=1.O.C([O-])(O)=O.[Na+]>COCCOC.ClCCl>[CH3:8][O:9][C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13]([C:2]2[N:3]=[C:4]([CH3:7])[S:5][CH:6]=2)=[CH:12][N:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-bromo-2-methyl-1,3-thiazole (commercially available from Frontier, 300 mg, 1.685 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (97 mg, 0.084 mmol) was added and the reaction mixture was stirred at room temperature for 15 min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 651 mg, 3.54 mmol) and 1M/H2O sol. of NaHCO3 (4.60 ml, 4.60 mmol) were added thereto. The reaction mixture was heated at 90° C. for 2.5 h and left at room temperature overnight. The mixture was then diluted with dichloromethane (20 ml) and washed with water (20 ml). The organic layer was separated through an hydrophobic frit and concentrated. The obtained crude was purified by flash chromatography eluting with Cyclohexane/AcOEt 8/2. 290 mg of the title compound were isolated as a white solid.

Workup

additionwere added
washwashed with water (20 ml)
customThe organic layer was separated through an hydrophobic frit
concentrationconcentrated
customThe obtained crude
customwas purified by flash chromatography
washeluting with Cyclohexane/AcOEt 8/2

Sources & evidence

ORD record: ord-ccc0413084de4899a032057559aca432
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178549B2

Reaction notes

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