Methanol → 9-benzyloxy-2-isopropyl-6-(3-phenyl-pyridin-2-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169237Notes

Reaction equation

HRID 2169237 reaction equation
O[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:27][CH:26]=[CH:25][N:24]=2)[N:8]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>O1CCCC1.ClCCl>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2[C:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:27][CH:26]=[CH:25][N:24]=2)[N:8]2[CH2:2][CH2:3][N:4]([CH:35]([CH3:36])[CH3:37])[C:5](=[O:6])[C:7]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 178457454HCID 178457454, compound

Product 1

HCID 867258869-benzyloxy-2-isopropyl-6-(3-phenyl-pyridin-2-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 35.23%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (166) in tetrahydrofuran (20 mL) were added triphenyl phosphine (66 mg, 0.25 mL) and DTAD (58 mg, 0.25 mmol) at room temperature. A yellow clear solution was formed, which was sonicated for 20 min. It was stirred at room temperature for 24 h. Silica thin layer chromatography was performed (5% methanol in dichloromethane, Rf=0.2). The mixture was concentrated under reduced pressure to get a crude product, which was purified by a preparative thin layer chromatography plate (mobile phase 5% methanol in dichloromethane) to get pure 9-benzyloxy-2-isopropyl-6-(3-phenyl-pyridin-2-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (167) (17 mg, 35.23%) as a yellow sticky solid.

Workup

  1. customA yellow clear solution was formed
  2. customwhich was sonicated for 20 min
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto get a crude product, which
  5. customwas purified by a preparative thin layer chromatography plate (mobile phase 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b99120fec9cb4a478468e1be5b38ab56
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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