Acetic Acid → 2-((2-(tert-Butyldimethylsilyloxy)ethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one

HRID 588713Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1.[Si:14]([O:21][CH2:22][CH:23]=O)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C([BH3-])#N.C(O)(=O)C>CN(C=O)C>[Si:14]([O:21][CH2:22][CH2:23][NH:1][CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 2-(aminomethyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (50 mg, 0.28 mmol) and 2-(tert-butyldimethylsilyloxy)acetaldehyde (53 uL, 0.28 mmol) in DMF (1 mL) was added siliabond cyanoborohydride (300 mg, 0.30 mmol, 1 mmol/g) and acetic acid (0.158 mL, 2.8 mmol). The mixture was heated via microwave at 150° C. for 5 minutes, concentrated in vacuo and the resulting material was purified via HPLC to provide the title compound (10 mg, 11% yield). 1H NMR (400 MHz, CDCl3) δ 4.51 (s, 2 H), 3.87 (t, J=5.5 Hz, 2H), 3.71 (s, 2H), 3.58-3.68 (m, 2H), 2.62 (ddd, J=14.7, 5.3, 5.1 Hz, 4H), 0.82 (s, 9H), 0.00 (s, 6H). Retention time=1.52 min.

Workup

concentrationconcentrated in vacuo
customthe resulting material was purified via HPLC

Sources & evidence

ORD record: ord-28f9562c84564b788c1d4dbae3cc5a55
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227982B2

Reaction notes

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