Potassium Phosphate, Tribasic → Ethyl 2-chloro-4-(2-chlorophenyl)pyrimidine-5-carboxylate

HRID 1036624Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[N:7]=[C:6]([C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:14])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

In a microwave tube was added 1 eq. of ethyl 2,4-dichloropyrimidine-5-carboxylate (200 mg, 0.91 mmol), 0.5 eq. of 3-chlorophenyl boronic acid (67 mg), 0.1 eq. of Pd2(dba)3 (83 mg), 3 eq. of K3PO4 in 4 mL of Dioxane. To this solution was added 1 eq. of tri-(t-butyl) phospine. The reaction was heated in the microwave to 160° C./300 W/for 1200 sec. The crude product was purified by prep HPLC. ES+=296.8.

Workup

customThe crude product was purified by prep HPLC

Sources & evidence

ORD record: ord-2ab0dd5998aa41dc89a6e72f09f10e91
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546414B2

Reaction notes

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