Methyl iodide → HCID 22560081, compound

HRID 983426Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[N:23]=[C:22]([Cl:24])[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25]I.[H-].[Na+]>CN(C=O)C>[CH3:25][N:17]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[N:9]=[CH:10]2)[C:18]1[N:23]=[C:22]([Cl:24])[N:21]=[CH:20][N:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To (1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine (473 mg, 1.40 mmol) in DMF (7.5 ml) at 0° C. was added MeI (0.262 mL, 4.21 mmol), followed by NaH (60% dispersion in oil)(67.4 mg, 1.69 mmol). The resulting mixture was stirred at 0° C. for 4.25 h. An additional 10 mg NaH was added after 3.1 h as TLC indicated remaining starting material. At this point, the reaction mixture was quenched with sat'd aq NH4Cl and diluted with water and EtOAc. The organic layer was washed with water and brine. The aqueous layer and washings were extracted once with EtOAc. The combined organics were dried, concentrated and purified by chromatography (SiO2, elution with 1:1 EtOAc-hexanes) to give N-methyl-(1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine as a pale oil: MS m/z=351 [M+H]+. Calc'd for C18H15ClN6: 350.10.

Workup

customAt this point, the reaction mixture was quenched with sat'd aq NH4Cl
additiondiluted with water and EtOAc
washThe organic layer was washed with water and brine
extractionThe aqueous layer and washings were extracted once with EtOAc
customThe combined organics were dried
concentrationconcentrated
custompurified by chromatography (SiO2, elution with 1:1 EtOAc-hexanes)

Sources & evidence

ORD record: ord-596db67dd0cb4687b575592e9e80d304
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864255B2

Reaction notes

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