3-Fluoroaniline → HCID 5328069, compound

HRID 2256129Notes

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

Participants

Reactant 2

HCID 97423-Fluoroaniline

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

Product 1

HCID 5328069HCID 5328069, compoundYield 65%

Conditions

Temperature: 160 °C

Procedure

A mixture of 7-amino-4 -methylthiopyrido[4,3-d]pyrimidine (215 mg, 1.12 mmol) and 3-fluoroaniline (1.16 g, 10.4 mmol) is stirred at 160° C. for 30 min. The resulting product is chromatographed over silica gel (6-7% MeOH/CH2Cl2) to give 7-amino-4-(3-fluoroanilino)pyrido[4,3-d]pyrimidine (185 mg, 65%) as a white solid. 1H NMR (DMSO) δ 9.94 (1H, brs), 9.36 (1H, s), 8.46 (1H, s), 7.91 (1H, brd, J=11.9 Hz), 7.63 (1H, brd, J=8.1 Hz), 7.41 (1H, dd, J=15.7, 7.7 Hz), 6.93 (1H, dt, Jt =8.5 Hz, J =2.4 Hz), 6.68 (2H, brs), 6.38 (1H, s).

Workup

customThe resulting product is chromatographed over silica gel (6-7% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-b9f18cbf59044fefa2b62a8912c3a668
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654307

Reaction notes

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