Hexafluoroacetylacetone → 4,6-Bis(trifluoromethyl)pyrimidin-2-amine

HRID 1284408Notes

Reaction equation

HRID 1284408 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[F:9][C:10]([F:21])([F:20])[C:11](=O)[CH2:12][C:13](=O)[C:14]([F:17])([F:16])[F:15].CCOCC.CCCCCC>CS(C)=O>[F:9][C:10]([F:20])([F:21])[C:11]1[CH:12]=[C:13]([C:14]([F:15])([F:16])[F:17])[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 3

HCID 73706HexafluoroacetylacetoneHCID 286947Carbonic acid-guanidine (1:1)HCID 21584099Diethylether hexane

Product 1

HCID 135599404,6-Bis(trifluoromethyl)pyrimidin-2-amineYield 49.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of guanidine carbonate (180 mmol) and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (120 mmol) was dissolved in 60 ml of DMSO and warmed to 110° C. for 2 to 3 hours. Flash chromatography of the crude reaction product with ether/hexane (50:50) afforded 13.8 g of the title compound as a white crystalline solid, m.p. 94.5°-96° C. NMR (60 MHz, CDCl3): δ 6.5 (br. s, 2H); 7.2 (s, 1H). A second product isolated was the hydroxypyrimidine (A is A-3): m.p. 116°-118.5° C. NMR (90 MHz, CDCl3): δ 7.1 (br. s, 3H); 7.3 (s, 1H).

Sources & evidence

ORD record
ord-fb62939153f142898162962e0b2b9e4d
Source dataset
uspto-grants-1986_01
Patent number
US04563211

Reaction notes

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