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

HRID 2169439Notes

Reaction equation

HRID 2169439 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([N:22]3[C:26]4=[N:27][CH:28]=[CH:29][CH:30]=[C:25]4[CH:24]=[CH:23]3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:31][CH2:32][N:33]([CH3:36])[C:34](=[O:35])[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([N:22]3[C:26]4=[N:27][CH:28]=[CH:29][CH:30]=[C:25]4[CH:24]=[CH:23]3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:31][CH2:32][N:33]([CH3:36])[C:34](=[O:35])[C:10]=12

Participants

7

Reactant 3

HCID 887MethanolHCID 867260709-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 867260719-hydroxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 80.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 9-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (407) (60 mg, 0.12 mmol) in ethanol (10 mL) was degassed, Pd—C (10%) (6 mg) added and hydrogenated for 40 min (hydrogen bludder) (TLC, 5% methanol in dichloromethane, Rf=0.2). The catalyst was filtered of and washed with 10% dichloromethane in ethanol (3×20 mL). The combined solvents were concentrated and the resulting sticky solid was washed with pentane to get pure 9-hydroxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (408) (38 mg, 78%) as an off-white solid.

Workup

  1. filtrationThe catalyst was filtered of and
  2. washwashed with 10% dichloromethane in ethanol (3×20 mL)
  3. concentrationThe combined solvents were concentrated
  4. washthe resulting sticky solid was washed with pentane

Sources & evidence

ORD record
ord-0d969797217d4d4592ae2bdd34521c67
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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