AcOH THF water → HCID 72548726, compound

HRID 1486551Notes

Reaction equation

HRID 1486551 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11](=[O:27])[N:12]([CH3:26])[C:13](=[O:25])[N:14]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:17])[CH:15]=1)(C(C)(C)C)(C)C.CC(O)=O.C1COCC1.O>O>[CH2:19]([NH:18][C:16]([N:14]1[CH:15]=[C:10]([CH2:9][OH:8])[C:11](=[O:27])[N:12]([CH3:26])[C:13]1=[O:25])=[O:17])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 21877175AcOH THF waterHCID 131736789HCID 131736789, compound

Product 1

HCID 72548726HCID 72548726, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-[[tert-Butyl(dimethyl)silyl]oxymethyl]-N-hexyl-3-methyl-2,4-dioxo-pyrimidine-1-carboxamide (0.05 g, 0.13 mmol) was treated with AcOH/THF/H2O (3 mL, 4:1:1) at room temperature. The reaction was stirred for 22 hrs. Water (3 mL) was added, and the solution extracted with EtOAc/cyclohexane 1:1 (3×6 mL). The combined organic phases were concentrated to approx. 1 mL, which was then diluted with dichloromethane (1.5 mL) and injected onto a 4 g SiO2 column followed by purification by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 70:30) to afford the title compound (0.033 g, 88%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.90 (t, J=6.8 Hz, 3H), 1.28-1.38 (m, 6H), 1.55-1.65 (m, 2H), 2.53 (bs, 1H), 3.38 (s, 3H), 3.39 (td, J=6.9, 5.8 Hz, 2H), 4.48 (s, 2H), 8.44 (bs, 1H), 9.26 (t, J=4.5 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 14.15, 22.66, 26.67, 28.06, 29.30, 31.53, 41.47, 59.62, 114.39, 133.97, 150.22, 152.31, 162.77. MS (ESI) m/z: 284 [M-H]+.

Workup

  1. extractionthe solution extracted with EtOAc/cyclohexane 1:1 (3×6 mL)
  2. concentrationThe combined organic phases were concentrated to approx. 1 mL, which
  3. additionwas then diluted with dichloromethane (1.5 mL)
  4. customfollowed by purification by column chromatography

Sources & evidence

ORD record
ord-5f63a2056566462bb19498a4fcee8426
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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