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

HRID 394751ノート

反応式

HRID 394751 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.).

後処理

  1. stirringstirred for another hour

出典と根拠

ORDレコード
ord-07d8bb5fa05b416080ee0a5485bb6652
出典データセット
uspto-grants-2003_08
特許番号
US06602863B1

反応ノート

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