Methyl iodide → 6-(3-fluorophenyl)-N-methylpyrido[3,2-d]pyrimidin-4-amine

HRID 1049912Notes

Reaction equation

HRID 1049912 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:18])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:22]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][CH3:22])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 867039146-(3-Fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

Product 1

HCID 867039156-(3-fluorophenyl)-N-methylpyrido[3,2-d]pyrimidin-4-amine

Procedure

Following the same reaction and purification procedure, the amine 1 (150 mg, 0.62 mmol) was treated with sodium hydride 60% dispersion in mineral oil (37 mg, 0.94 mmol) and iodomethane (0.04 mL, 0.62 mmol) to provide 6-(3-fluorophenyl)-N-methylpyrido[3,2-d]pyrimidin-4-amine 26. LC/MS (ESI+): m/z 255 (M+H). 1H NMR (400 MHz, DMSO) δ 8.89 (s, 1H), 8.38-8.19 (m, 1H), 8.19-8.03 (m, 3H), 7.96 (d, J=8.5 Hz, 1H), 7.58 (dd, J=14.3, 7.8 Hz, 1H), 7.32 (dd, J=10.1, 8.0 Hz, 1H), 3.49 (s, 3H).

Workup

  1. customthe same reaction and purification procedure

Sources & evidence

ORD record
ord-4524e372703b4270a24ad8782a0b7500
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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