Potassium Phosphate, Tribasic → (E)-4-chloro-6-(4-chlorostyryl)pyrimidine

HRID 2059878Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:20]=[CH:19][C:13](/[CH:14]=[CH:15]/B(O)O)=[CH:12][CH:11]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:6]1[CH:7]=[C:2](/[CH:15]=[CH:14]/[C:13]2[CH:19]=[CH:20][C:10]([Cl:9])=[CH:11][CH:12]=2)[N:3]=[CH:4][N:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of commercially available 4,6-dichloropyrimidine (300 mg, 2.01 mmol), (E)-4-chlorostyrylboronic acid (441 mg, 2.41 mmol), potassium phosphate (1282 mg, 6.04 mmol), and PalladiumTetrakis (116 mg, 0.10 mmol) in DMF (1 mL) was stirred under nitrogen at 40° C. for 2 days. The reaction was filtered, diluted with CH2Cl2, washed with water, brine, dried (MgSO4), and concentrated. The crude product was purified using ISCO flash chromatography (silica gel/hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product (E)-4-chloro-6-(4-chlorostyryl)pyrimidine 20A (120 mg, 0.49 mmol, 23.73% yield) as a light yellow solid. LC/MS 252 (M+H)+, tR 1.07 min (method 5).

Workup

filtrationThe reaction was filtered
additiondiluted with CH2Cl2
washwashed with water, brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude product was purified

Sources & evidence

ORD record: ord-5c24e7569c4f40c9ba07ab9d1abe1618
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278316B2

Reaction notes

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