Diisopropylethylamine → ethyl 2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-methylpyrimidine-5-carboxylate

HRID 339997Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1B1OC(C)(C)C(C)(C)O1.Cl[C:18]1[N:23]=[C:22]([CH3:24])[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][N:19]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1[C:18]1[N:23]=[C:22]([CH3:24])[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][N:19]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-chloro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.45 g, 5.98 mmol), ethyl 2-chloro-4-methylpyrimidine-5-carboxylate (0.999 g, 4.98 mmol), bis(tri-t-butylphosphine)palladium (509 mg, 0.996 mmol), and N,N-diisopropylethylamine (1.74 mL, 9.98 mmol) in 1,4-dioxane (10 mL) and water (0.5 mL) was stirred at 110° C. for 40 mins under microwave. Direct purification by combi-flash chromatography afforded 0.83 g (59% yield) of the desired product. LC-MS found: 281.1 (M+H)+.

Workup

customDirect purification by combi-flash chromatography

Sources & evidence

ORD record: ord-640811577481449ea52aa1dd4167d370
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895571B2

Reaction notes

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