Dimethylformamide → (2R,3R)-2-((4-Acetamido-2-oxo-pyrimidin-1(2H)-yl)methyl)butane-1,3-diol

HRID 1754605Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8](O)[CH2:9][CH:10]([OH:12])[CH3:11])[C:4](=[O:14])[N:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].CN([CH:25]=[O:26])C>>[C:15]([NH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C@@H:9]([C@H:10]([OH:12])[CH3:11])[CH2:25][OH:26])[C:4](=[O:14])[N:3]=1)(=[O:17])[CH3:16]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 7918Acetic Anhydride

HCID 131733670(4-Amino-2-oxo-pyrimidin-1(2H)-yl)butane-1,3-diol

Product 1

HCID 90411135(2R,3R)-2-((4-Acetamido-2-oxo-pyrimidin-1(2H)-yl)methyl)butane-1,3-diolYield 108%

Procedure

To a solution of 20 (0.5 g, 2.34 mmol) in 12 ml of anhydrous DMF was added dropwise with stirring 0.243 ml (2.57 mmol) of acetic anhydride. The reaction was kept at room temperature for 3 days and then concentrated. The oily residue was dried by co-evaporation with xylene and then in vacuo to afford 0.65 g (108%) of 21 (contaminated with some DMF) as a white solid, which was sufficiently pure to be used in the next step without additional purification. 1H NMR (DMSO-d6): δ 10.81 (s, 1H), 8.00 (d, J=7.2 Hz, 1H), 7.13 (d, J=7.2 Hz, 1H), 4.62 (d, J=5.1 Hz, 1H), 4.53 (t, J=4.8 Hz, 1H), 4.02 (m, 1H), 3.73 (m, 2H), 3.53 (m, 2H), 2.09 (s, 3H), 1.80 (m, 1H), 1.10 (d, J=6.3 Hz, 3H).

Workup

concentrationconcentrated
dry with materialThe oily residue was dried by co-evaporation with xylene

Sources & evidence

ORD record: ord-0ea934e09db84a6a91981384e2139dc9
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169256B2

Reaction notes

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