Benzylamine → N-[4-(benzylamino)pyrido[4,3-d]pyrimidin-7-yl]acetamide

HRID 50818Notes

Reaction equation

[C:1]([NH:4][C:5]1[N:14]=[CH:13][C:12]2[C:11](SC)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:1]([NH:4][C:5]1[N:14]=[CH:13][C:12]2[C:11]([NH:24][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 7504Benzylamine

HCID 105376457-Acetylamino-4-methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328248N-[4-(benzylamino)pyrido[4,3-d]pyrimidin-7-yl]acetamideYield 62%

Conditions

Temperature: 140 °C

Procedure

A mixture of 7-acetylamino-4-methylthiopyrido[4,3-d]pyrimidine (0.40 g, 1.71 mmol) and benzylamine (1.0 mL, 9.15 mmol) is stirred under N2 at 140° C. For 1 h, and the resulting product is chromatographed on silica gel (EtOAc) to give 7-acetylamino-4-benzylaminopyrido[4,3-d]pyrimidine (0.31 g, 62%) as a white solid. 1H NMR (DMSO) δ 10.79 (1H, s), 9.42 (1H, s), 9.23 (1H, t, J=5.8 Hz), 8.49 (1H, s), 8.18 (1H, s), 7.39 (1H, dt, Jd=6.9 Hz, Jt=1.7 Hz), 7.34 (1H, tt, J=7.3, 1.7 Hz), 7.25 (1H, tt, J=7.1, 1.7 Hz), 4.80 (2H, d, J=5.8 Hz), 2.15 (3H, s)

Workup

customthe resulting product is chromatographed on silica gel (EtOAc)

Sources & evidence

ORD record: ord-49e47e3f41be43b98c2e883c00b76edf
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Reaction notes

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