Tetrabutylammonium Fluoride → 4-Hydroxy-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]-5-methylpyrimidin-2(1H)-one

HRID 582525Notes

Reaction equation

HRID 582525 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][O:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][O:21]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15659235HCID 15659235, compound

Product 1

HCID 4515934-Hydroxy-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]-5-methylpyrimidin-2(1H)-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9 (93.3 mg, 0.2 mmole) in tetrahydrofuran (THF) (3 ml) was added a 1.0 M solution of tetra-n-butylammonium fluoride in THF (0.24 ml, 0.24 mmole) and the mixture stirred at room temperature for 1 hour. The mixture was then concentrated and purified by column chromatography over silica gel to yield 11 (42 mg, 92.1%) as white solid: [α]25D-18.8° (C o.17, MeOH); 1H NMR (DMSO-d6) δ 1.75 (d, J=1.2 Hz, 3H, CH3), 3.63 (dd, J+6.0, 2.6 Hz, 2H, CH2OH), 4.03 (dd, J=9.9, 5.5 Hz, 1H, 5-H), 4.22 (dd, J=9.9, 2.0 Hz, 1H, 5-H), 4.90 (t, J=2.6 Hz, 1H, 2-H), 5.16 (t, J-t.0 Hz, 1H, OH), 6.21 (dd, J=5.5, 2.0 Hz, 1H, 4-H), 7.67 (d, J=1.2 Hz, 1H, 6'-H), 11.27 (br s, 1H NH); UV (H2) max 266.0 (ε 10757); 266.5 (ε 9894) (pH 2); 266.3 (ε 8397) (pH 11); Anal. Calcd for C9H12O5N2 : C, 47.36; H, 5.31; N, 12.28. found: c, 47.28; H, 5.34; N, 12.29.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by column chromatography over silica gel

Sources & evidence

ORD record
ord-00120fb6701a4428b594faf0f8fa9e47
Source dataset
uspto-grants-1999_07
Patent number
US05925643

Reaction notes

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