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

HRID 507473Notes

Reaction equation

HRID 507473 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:30])[CH:28]=[CH2:29].CO.CCOC(C)=O>C1COCC1.CN(C1C=CN=CC=1)C>[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:30])[CH:28]=[CH2:29])[N:19]=[CH:18][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chloride2×HCID 53282584-N-(3-bromophenyl)pyrido[3,4-d]pyrimidine-4,6-diamineHCID 21584119Ethylacetate methanol2×

Product 1

HCID 5329069N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}prop-2-enamideYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)amino]-pyrido[3,4-d]pyrimidine (J Med Chem, 1996;39:1823) (455 mg, 1.50 mmol) in dry THF (50 mL) at 0° C. under N2 was added Et3N (22.5 mmol, 1.61 mL), a catalytic amount of DMAP (45 mg) and acryloyl chloride (4.50 mmol, 366 μL). The reaction mixture was stirred for 1 hour and then additional acryloyl chloride (100 μL) was added and the reaction was allowed to warm to room temperature and stirred for another hour before being worked up as in the previous example, to give after column chromatography on silica gel eluting with MeOH/EtOAc (5:95), N-[4-[(3-bromophenyl)amino]pyrido-[3,4-d]pyrimidin-6-yl]acrylamide (20 mg, 37%) as a cream powder, mp (EtOAc/MeOH) 238-245° C. (dec.).

Workup

  1. stirringstirred for another hour

Sources & evidence

ORD record
ord-88e577cef9c94a21a9f5515a2da8f646
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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