Dimethyl Sulfoxide → HCID 54692314, compound

HRID 1162834Notes

Reaction equation

HRID 1162834 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:25][CH2:24][N:10]3[C:11](=[O:23])[N:12]([CH:17]4[CH2:22]CSC[CH2:18]4)[C:13](=[O:16])[C:14]([OH:15])=[C:9]3[C:8]2=[O:26])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:34].[CH3:40][S:41]([CH3:43])=[O:42]>ClCCl>[O:42]=[S:41]1(=[O:34])[CH2:43][CH2:22][CH:17]([N:12]2[C:13](=[O:16])[C:14]([OH:15])=[C:9]3[C:8](=[O:26])[N:7]([CH2:6][C:5]4[CH:27]=[CH:28][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:25][CH2:24][N:10]3[C:11]2=[O:23])[CH2:18][CH2:40]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 54676801HCID 54676801, compound

Product 1

HCID 54692314HCID 54692314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-fluorobenzyl)-9-hydroxy-7-tetrahydro-2H-thiopyran-4-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (30 mg, 0.074 mmol, Example 36). in dichloromethane (2 mL) was added 3-Chloroperoxybenzoic acid (38 mg, 0.165 mmol). The reaction was stirred at room temperature and after one hour DMSO was added (0.2 mL). After stirring for one hour, the dichloromethane was evaporated under a stream of nitrogen and the reaction was diluted with water and aq. NaHCO3. The precipitated product was collected by filtration and rinsed with water and diethyl ether. Drying under high vacuum provided the title compound. 1H NMR (400 MHz, CDCl3) δ 11.8 (s, 1H), 7.3 (m, 2H), 7.07 (t, J=8.6 Hz, 2H), 5.07 (tt, J=12.0, 3.2 Hz, 1H), 4.69 (s, 2H), 4.00 (t, J=5.6 Hz, 2H), 3.53 (t, J=5.6 Hz, 2H), 3.35 (m, 2H), 3.16 (m, 4H), 1.95 (m, 2H).

Workup

  1. additionwas added (0.2 mL)
  2. customthe dichloromethane was evaporated under a stream of nitrogen
  3. additionthe reaction was diluted with water and aq. NaHCO3
  4. filtrationThe precipitated product was collected by filtration
  5. washrinsed with water and diethyl ether
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-987d9279a1144a4580158933557b7a71
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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