Methanol → 9-hydroxy-2-methyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169479Notes

Reaction equation

HRID 2169479 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:28][CH2:29][N:30]([CH2:33]C3CC3)[C:31](=[O:32])[C:10]=12)C1C=CC=CC=1.[H][H].CO>C(O)C.ClCCl.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:19][CH2:20][CH2:21]2)[N:11]2[CH2:28][CH2:29][N:30]([CH3:33])[C:31](=[O:32])[C:10]=12

Participants

7

Reactant 3

HCID 887MethanolHCID 867261069-benzyloxy-2-cyclopropylmethyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 867261039-hydroxy-2-methyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 91.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 9-benzyloxy-2-cyclopropylmethyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (448) (40 mg, 0.083 mmol) in ethanol (3 mL), Pd—C (10%, w/w, 10 mg) was added. The reaction mixture was allowed stir for 1 h in a hydrogen atmosphere at balloon pressure while silica thin layer chromatography was performed (10% methanol in dichloromethane; Rf=0.3). After completion of the reaction, the reaction mixture was filtered through a celite bed and concentrated. The resulting crude product was triturated with 70% ethyl acetate in hexane to get 9-hydroxy-2-methyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (449) (27 mg, 83%) as an off-white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through a celite bed
  3. concentrationconcentrated
  4. customThe resulting crude product was triturated with 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4bb438198b7648888494db164aa1ceb9
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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