Triethylamine → N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}-2-methylprop-2-enamide

HRID 394753Notes

Reaction equation

HRID 394753 reaction equation
[NH2:1][C:2]1[N:19]=[CH:18][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=3)[C:4]=2[CH:3]=1.CCN(CC)CC.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29].CCOC(C)=O.C(Cl)Cl>CN(C1C=CN=CC=1)C.C1COCC1.C(Cl)Cl.CCCCCC>[Br:17][C:13]1[CH:12]=[C:11]([NH:10][C:9]2[C:4]3[CH:3]=[C:2]([NH:1][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])[N:19]=[CH:18][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 53282584-N-(3-bromophenyl)pyrido[3,4-d]pyrimidine-4,6-diamineHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 5329071N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}-2-methylprop-2-enamideYield 6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)-amino]pyrido[3,4-d]pyrimidine (J Med Chem, 1996;39:1823) (250 mg, 0.82 mmol), Et3N (excess, 2.0 mL) and DMAP (catalytic) in THF (30 mL) under nitrogen was added methacryloyl chloride (3×1.1 mol eq., total of 264 μL), the reaction conditions and work up were followed as above to give after column and preparative layer chromatography on silica gel eluting with EtOAc/CH2Cl2 (1:1), N-[4-[(3-bromophenyl)amino]-pyrido-[3,4-d]pyrimidin-6-yl]-2-methylacrylamide (18 mg, 6%) as a cream powder, mp (CH2Cl2/hexane) 177-178° C.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-68726ddc595148daafe3ae62f6fa68f3
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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