Triethylamine → Pyrido[2,3-d]pyrimidine

HRID 1614169Notes

Reaction equation

HRID 1614169 reaction equation
C(OC(=O)[C@H:5]([CH2:7][CH2:8][C:9](OCC)=O)[NH2:6])C.S(Cl)(Cl)=O.Cl.C(OC(=O)[C@H:24](CCC(OCC)=O)[NH2:25])C.[CH2:34]([N:36](CC)[CH2:37]C)C>CN(C)C1C=CN=CC=1>[N:25]1[C:24]2[N:6]=[CH:5][CH:7]=[CH:8][C:9]=2[CH:37]=[N:36][CH:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 73960Glutamic acid diethyl ester hydrochlorideHCID 73961Glutamic acid diethyl ester

Product 1

HCID 582898Pyrido[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Those compounds of the present invention where R2 is prop-1,3-diyl are prepared by first preparing a benzoic acid derivative described above having a p-propen-1-yl group using the oxazoline described in Meyers, Acc. Chem. Res., 14, 375 (1978), which is incorporated herein by reference. Acid hydrolysis (5N HCl, reflux, 36 hours) affords 4-allylbenzoic acid which is converted to the corresponding diethyl-L-glutamate derivative by initial treatment with thionyl chloride (4.0 eqv., benzene, reflux, 4 hours) followed by diethyl-L-glutamate hydrochloride (2.1 equivalents), 4-dimethylamino-pyridine (0.01 eqv.) and triethylamine (18 hours). Coupling to either the pyrrolo- or pyrido[2,3-d]pyrimidine, at least by Alternative 2, affords the compounds of the present invention where R2 is a propen-1,3-diyl.

Sources & evidence

ORD record
ord-3417de9f33004b0a9ba985cd79f0f76c
Source dataset
uspto-grants-1993_03
Patent number
US05196424

Reaction notes

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