2023_BG_11B_1 - Hydrolysis on 2-amino-4-methylpyridine fragment

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Reaction scheme

Outcome

4.968 g (29.7 mmol, 93%)

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1. Dissolved SM (8.690 g, 32.0 mmol) in NaOH (2.5 M, 30 mL)
2. Heated to 80 C from 10.25 am.

TLC indicated completion after ~45 minutes.

Work up as usual - see Step 2.

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Vial: 15.2925 Full vial: 20.2605 Mass: 4.968 g (29.7 mmol, 93%)

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H NMR

1H NMR (300 MHz, DMSO) δ 10.65 (s, 1H), 10.44 (s, 1H), 8.83 (s, 1H), 8.11 (d, 1H), 6.99 (s, 1H), 6.90 (d, 1H), 2.28 (s, 3H).

2023_BG_11B_1_1.zip 2023_BG_11B_1.pdf

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LRMS

Peaks at 168.16 [M+H]+, 190.11 [M+Na]+, 166.02 [M-H]-

2023_BG_11B_1.pdf 2023_BG_11B_1.d.zip

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NMR

1H NMR (500 MHz, DMSO-d6) δ 10.67 – 10.63 (m, 1H), 10.46 – 10.42 (m, 1H), 8.82 (s, 1H), 8.09 (d, J = 5.2 Hz, 1H), 7.00 – 6.96 (m, 1H), 6.89 (dd, J = 5.4, 1.5 Hz, 1H), 2.27 (s, 3H).

13C NMR (126 MHz, DMSO) δ 182.59, 181.15, 154.20, 150.14, 146.13, 128.37, 124.59 (d), 119.72, 116.22 (d), 113.03, 21.26.

2023_BG_11B 500 MHz.pdf 230709_11B_1.zip 230709_11B_2.zip