Tetrahydrofuran → (8R,10R)-10-(5-Chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-phenyl-7,8,9,10-tetrahydropyrazino[1',2':1,2]pyrrolo[3,4-d]pyrimidine-2,4(1H,3H)-dione

HRID 624567Notes

Reaction equation

HRID 624567 reaction equation
[BH4-].[Na+].C(O[C:11]([NH:13][CH:14]([CH2:19][N:20]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:27]2[C:22]([N:23]([CH3:38])[C:24](=[O:37])[N:25]([CH3:36])[C:26]2=[O:35])=[CH:21]1)[C:15](OC)=[O:16])=O)C1C=CC=CC=1.[Cl-:39].[Li+].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>CCO>[Cl:39][C:45]1[O:44][C:43]([C@H:11]2[C:21]3=[C:22]4[C:27](=[C:28]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:20]3[CH2:19][C@H:14]([CH2:15][OH:16])[NH:13]2)[C:26](=[O:35])[N:25]([CH3:36])[C:24](=[O:37])[N:23]4[CH3:38])=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86722890Methyl 2-(((benzyloxy)carbonyl)amino)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate

Product 1

HCID 86722891(8R,10R)-10-(5-Chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-phenyl-7,8,9,10-tetrahydropyrazino[1',2':1,2]pyrrolo[3,4-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.234 g, 6.20 mmol) was added to a solution of methyl 2-(((benzyloxy)carbonyl)amino)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate (1.52 g, 3.10 mmol) and lithium chloride (0.263 g, 6.20 mmol) in THF (79 ml) and EtOH (39.7 ml) at 0° C. The mixture was stirred at room temperature for 16 hours. The reaction was quenched with saturated NaHCO3(aq) (20 mL), diluted with water (50 ml) and extracted with DCM (3×150 ml). The combined organic extracts were diluted with MeOH (50 ml), dried over sodium sulfate, passed through a hydrophobic frit and evaporated under vacuum to afford the title compound and was a by-product. The resulting mixture was taken forward to the next step without further purification.

Workup

  1. customThe reaction was quenched with saturated NaHCO3(aq) (20 mL)
  2. additiondiluted with water (50 ml)
  3. extractionextracted with DCM (3×150 ml)
  4. additionThe combined organic extracts were diluted with MeOH (50 ml)
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-32b086d9f1444913aee537e1bde2a6e2
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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