Pyrimidin-5-amine → Ethyl 6-methyl-3-(5-pyrimidinylamino)-2-pyridinecarboxylate

HRID 2219573Notes

Reaction equation

HRID 2219573 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](Br)=[CH:10][CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:5])[CH3:2].[NH2:14][C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1>[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)=[CH:10][CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 344373Pyrimidin-5-amineHCID 69237506Ethyl 3-bromo-6-methylpicolinate

Product 1

HCID 58368053Ethyl 6-methyl-3-(5-pyrimidinylamino)-2-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The Pd catalyzed coupling of 3-Bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester and 5-Amino-pyrimidine (CAS:[591-55-9] (J. Org. Chem., 20, 829 (1955)) was performed in accordance with the general method of Example 78, step 3 to yield the tide compound as a light brown solid, MS (ISP): m/e=259.3 (M+H+).

Sources & evidence

ORD record
ord-03c5d9c132504ddcae3956b1aa584b3d
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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