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

HRID 499249
Notes
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Reaction equation

HRID 499249 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 59421209Ethyl 2-chloro-4-(2-chlorophenyl)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

In a microwave tube was added 1 eq. of ethyl 2,4-dichloropyrimidine-5-carboxylate (200mg, 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

  1. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-dd3e307300ee42aeba3d477250e5de48
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767680B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes