Thymidine → HCID 70430213, compound

HRID 1789329Notes

Reaction equation

[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C([N:20]([CH2:23][CH3:24])CC)C.[C-:25]#N.C#C>>[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@:3]([CH:25]=[CH:24][C:23]#[N:20])([OH:4])[CH2:2]1

Participants

Reactant 3

HCID 5789Thymidine

HCID 8471Triethylamine

HCID 19103849HCID 19103849, compound

Product 1

HCID 70430213HCID 70430213, compound

Procedure

The title compound is obtained by following essentially the same method described in Example V. Thus starting from thymidine (360 mg, 1.5 mmol), triethylamine (210 μl, 1.5 mmol) and acetylene cyanide. (152 mg, 3 mmol), the title compound is obtained after purification on preparative TLC (5% methanol in ethyl acetate, Rf 0.45), as a slight yellow oil (140 mg, 35%) pure by TLC analysis. 1HNMR, (DMSO) 1.86 (s, 1H,-CH3 ) 6.17 (t,J=6.1 Hz, 1H, --O--CH--N) 6.18 (d, J=9 Hz, 1H, --CH=CH--CN) 7.06 (d,J=9 Hz, 1H, --CH=CH--CN) 7.89 (s,1H, N--CH=C--CH3).

Sources & evidence

ORD record: ord-4b6f99895a6949e0951fbb44073175d2
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689321

Reaction notes

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