Lithium Chloride → HCID 77106434, compound

HRID 2201217Notes

Reaction equation

HRID 2201217 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[O:8][C:7]([CH:9]2[C:14]3=[C:15]4[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[C:16]4=[C:17]([C:18]4[S:19][CH:20]=[C:21]([C:23](OCC)=[O:24])[N:22]=4)[N:13]3[CH2:12][CH2:11][S:10]2)=[CH:6][CH:5]=1.[Cl-].[Li+]>C(O)C.C1COCC1>[Cl:3][C:4]1[O:8][C:7]([CH:9]2[C:14]3=[C:15]4[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[C:16]4=[C:17]([C:18]4[S:19][CH:20]=[C:21]([CH2:23][OH:24])[N:22]=4)[N:13]3[CH2:12][CH2:11][S:10]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 433294Lithium Chloride2×HCID 4311764Sodium borohydride2×HCID 86723494HCID 86723494, compound

Product 1

HCID 77106434HCID 77106434, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (45.1 mg, 1.191 mmol) was added to a solution of ethyl 2-(10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazin-5-yl)thiazole-4-carboxylate (302 mg, 0.596 mmol) and lithium chloride (50.5 mg, 1.191 mmol) in ethanol (7.50 ml) and THF (15 ml) at 0° C. The mixture was warmed to room temperature and stirred for 7 hours. Further portions of lithium chloride (50.5 mg, 1.191 mmol) and sodium borohydride (45.1 mg, 1.191 mmol) were added to allow the reaction to run to completion. The reaction was quenched with saturated NaHCO3(aq) solution (50 ml), diluted with water (20 ml) and extracted with DCM (3×75 ml). The combined organic extracts were washed with water (20 ml), passed though a hydrophobic frit and evaporated under vacuum to afford the title compound.

Workup

  1. customthe reaction
  2. customThe reaction was quenched with saturated NaHCO3(aq) solution (50 ml)
  3. additiondiluted with water (20 ml)
  4. extractionextracted with DCM (3×75 ml)
  5. washThe combined organic extracts were washed with water (20 ml)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-50fec9fbce7a428eb8059343e38ff392
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…