Methyl iodide → 2-Methoxy-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine

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)=[O:12])#[N:2].[CH3:22]I>>[CH3:22][O:12][C:11]1[N:13]=[C:1]([NH2:2])[C:3]2[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=2[N:10]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 57456902N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide

Product 1

HCID 252243392-Methoxy-5,6-dimethylthieno[2,3-d]pyrimidin-4-amineYield 86%

Procedure

Prepared in a similar manner to Example 25 from N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide (Example 4a) and methyl iodide in 86% yield. 1H NMR (400 MHz, CDCl3) δ2.35 (s, 3H), 2.36 (s, 3H), 3.53 (s, 3H), 6.0 (bs, 2H). MS 210 (MH+).

Sources & evidence

ORD record: ord-999165459808454a92efc7421d31629e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541421B2

Reaction notes

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