Tris(furan-2-yl)phosphane → 2,4-Diamino-6-methyl-5-[3-(4-chlorophenyl)-3-oxo-1-propenyl]pyrimidine

HRID 54255

Reaction equation

HRID 54255 reaction equation
[O:1]=[C:2]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[CH:3]=[CH:4][Sn](CCCC)(CCCC)CCCC.[NH2:25][C:26]1[N:31]=[C:30]([NH2:32])[C:29](I)=[C:28]([CH3:34])[N:27]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN(C)C=O>[NH2:25][C:26]1[N:31]=[C:30]([NH2:32])[C:29]([CH:4]=[CH:3][C:2]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[O:1])=[C:28]([CH3:34])[N:27]=1

Participants

5

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 158557925-Iodo-6-methylpyrimidine-2,4-diamineHCID 676328951-Oxo-1-(4-chlorophenyl)-3-tributylstannyl-2-propene

Product 1

HCID 537941852,4-Diamino-6-methyl-5-[3-(4-chlorophenyl)-3-oxo-1-propenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound is prepared in a manner analogous to that of Step E of Example 4, using 2.9 grams of (0.0064 mole) of 1-oxo-1-(4-chlorophenyl)-3-tributylstannyl-2-propene, 1.2 grams (0.0048 mole) of 2,4-diamino-5-iodo-6-methylpyrimidine (prepared in Step B of Example 3), 0.04 gram of tri-2-furylphosphine and 0.04 gram (catalyst) of tris(dibenzylidineacetone)dipalladium(0) in 30 mL of N,N-dimethylformamide, yielding 2,4-diamino-6-methyl-5-[3-(4-chlorophenyl)-3-oxo-1-propenyl]pyrimidine.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step E of Example 4

Sources & evidence

ORD record
ord-971f2e7a68da453ba8b23abb58bd156e
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Linked notes

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