Benzylamine → HCID 178507216, 화합물

HRID 1059543노트

반응식

HRID 1059543 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[CH2:11](NC1C2N=CC=CC=2N=CN=1)C1C=CC=CC=1.C(N)C1C=CC=CC=1.C([O-])([O-])OCC.C(OC(=O)C)(=O)C.[SH-:50]>C(O)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:9](=[S:50])[NH:10][CH:11]=[N:8][C:6]=2[CH:7]=1

참가 물질

7

반응물 5

HCID 7504BenzylamineHCID 2958964,6-DiaminonicotinonitrileHCID 5047209HydrosulfideHCID 5328272N-benzylpyrido[3,2-d]pyrimidin-4-amineHCID 86583744Ethyl orthoformate acetic anhydride

생성물 1

HCID 178507216HCID 178507216, 화합물

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

2,4-Diamino-5-cyanopyridine can be cyclized directly to many 4-benzylaminopyridopyrimidine derivatives by treatment with the benzylamine and formic acid at high temperature. For less nucleophilic amines 2,4-diamino-5-cyanopyridine is converted via ethyl orthoformate/acetic anhydride treatment, followed by cyclization with hydrosulfide ion in anhydrous conditions, to give 7-amino-4-thiono-3H-pyrido[4,3-d]pyrimidine. S-Alkylation and displacement with an appropriate amine gives the desired product. If R4 is not amino, the amine can be acylated, or reductively alkylated. Alternatively 2,4-diamino-5-cyanopyridine can be hydrolysed to the corresponding amide, and this species can be cyclized to 7-amino-4-oxo-3H-pyrido[4,3-d]pyrimidine with orthoformate. Diazotization of the 7-amine and replacement with fluorine allows for introduction of other amine and alkoxide nucleophiles at the end of the synthesis after the C4 substituent has been introduced in the usual manner. Diazotization and replacement of the amine with bromide allows for Stille couplings at the 7-position.

출처 및 근거

ORD 기록
ord-8212e9ba927a4b8d828ffe5459e5f316
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521620B1

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