4-Aminoacetanilide → HCID 5328076, compound

HRID 1281935Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)=[O:16]>>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:24][C:21]3[CH:20]=[CH:19][C:18]([NH:17][C:15](=[O:16])[CH3:14])=[CH:23][CH:22]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 312304-Aminoacetanilide

HCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328076HCID 5328076, compoundYield 52%

Conditions

Temperature: 200 °C

Procedure

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (138 mg, 0.72 mmole) and 4-aminoacetanilide (1.50 g, 10.0 mmole) is stirred under N2 at 200° C. for 1 h. The resulting product is chromatographed over alumina (8-10% MeOH/CH2Cl2) to give 7-amino-4-(4-acetamidoanilino)pyrido[4,3-d]pyrimidine (110 mg, 52%) as a pale yellow solid. 1H NMR (DMSO) δ 9.94, 9.79 (1H, 1H, 2 brs), 9.31 (1H, s), 8.34 (1H, s), 7.69 (2H, d, J=8.9 Hz), 7.57 (2H, d, J=8.9 Hz), 6.57 (2H, brs), 6.43 (1H, s), 2.05 (3H, s).

Workup

customThe resulting product is chromatographed over alumina (8-10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-10358adb0c6e4794a6dd2dbfeaded9e5
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455534B2

Reaction notes

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