Piperidine → 2,4-Diamino-6-methyl-5-[3-(4-trifluoromethylphenyl)-3-methyl-1-butynyl]pyrimidine

HRID 54281Notes

Reaction equation

HRID 54281 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](I)=[C:4]([CH3:10])[N:3]=1.[CH3:11][C:12]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)([CH3:15])[C:13]#[CH:14].N1CCCCC1>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:14]#[C:13][C:12]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=2)([CH3:15])[CH3:11])=[C:4]([CH3:10])[N:3]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 153325731-(2-Methylbut-3-yn-2-yl)-4-(trifluoromethyl)benzeneHCID 158557925-Iodo-6-methylpyrimidine-2,4-diamine

Product 1

HCID 214679742,4-Diamino-6-methyl-5-[3-(4-trifluoromethylphenyl)-3-methyl-1-butynyl]pyrimidineYield 95.7%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Step C of Example 3, using 1.3 grams (0.005 mole) of 2,4-diamino-5-iodo-6-methylpyrimidine, 1.6 grams of (0.008 mole) of 3-methyl-3-(4-trifluoromethylphenyl)-1-butyne (prepared as in Step F of Example 17), 0.3 gram of bis(triphenylphosphine)palladium(II) chloride, 0.05 gram of copper iodide, and 8 mL of piperidine in 20 mL of N,N-dimethylformamide, yielding 1.6 grams of 2,4-diamino-6-methyl-5-[3-(4-trifluoromethylphenyl)-3-methyl-1-butynyl]pyrimidine, mp 153°-157° C. The NMR spectrum is consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step C of Example 3

Sources & evidence

ORD record
ord-3b8ecc79b52241c1addd6d1392a5f5ae
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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