2,4,6-Trichloropyrimidine → HCID 59198389, compound

HRID 1920825Notes

Reaction equation

HRID 1920825 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[N:20][C:21]([NH2:24])=[N:22][CH:23]=2)O1>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[N:20][C:21]([NH2:24])=[N:22][CH:23]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

Product 1

HCID 59198389HCID 59198389, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

According to Method 5, the reaction of 2,4,6-trichloropyrimidine with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine in the presence of Pd(dppf)Cl2-CH2Cl2 in DME and 2 M Na2CO3 (3:1) gave 2,6-dichloro-4,5′-bipyrimidin-2′-amine in 48% yield. LCMS (m/z): 241.1 (MH+), Rt 2.05 min.

Sources & evidence

ORD record
ord-9ffe40cd748d4e549feaf3046bcde133
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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