Methyl iodide → 5,6-Dimethyl-2-(methylthio)thieno[2,3-d]pyrimidin-4-amine

HRID 711632Notes

Reaction equation

[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11]([NH:13]C(=O)C1C=CC=CC=1)=[S:12])#[N:2].[OH-].[Na+].[CH3:24]I>C(O)C>[CH3:8][C:7]1[C:3]2[C:1]([NH2:2])=[N:13][C:11]([S:12][CH3:24])=[N:10][C:4]=2[S:5][C:6]=1[CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamothioyl)-benzamide (Example 1a) (1.33 g, 4.22 mmol) in ethanol (25 mL) was added NaOH (2.0 N, 5.8 mL) at room temperature under nitrogen. After stirring at 100° C. under nitrogen for 0.5 h, the reaction mixture was cooled in an ice bath and MeI (0.8 mL) was added dropwise. After stirring for another 0.5 h, the resulting precipitate was collected by filtration, rinsed with water, 20% EtOH/H2O, and dried under vacuum to give the title compound (840 mg, 89%). 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H), 2.34 (s, 3H), 2.42 (s, 3H), 6.93 (bs, 2H). MS 226 (MH+).

Workup

temperaturethe reaction mixture was cooled in an ice bath
stirringAfter stirring for another 0.5 h
filtrationthe resulting precipitate was collected by filtration
washrinsed with water, 20% EtOH/H2O
customdried under vacuum

Sources & evidence

ORD record: ord-ce97dc192a0743429143f51ced172dab
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

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