Lithium Chloride → 5-(4-(Hydroxymethyl)thiazol-2-yl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201318Notes

Reaction equation

HRID 2201318 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:9]2=[CH:10][N:11]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:12]([C:13]3[S:14][CH:15]=[C:16]([C:18](OCC)=[O:19])[N:17]=3)=[C:8]2[C:7](=[O:31])[N:6]([CH3:32])[C:5]1=[O:33].[Cl-].[Li+]>C(O)C.C1COCC1>[OH:19][CH2:18][C:16]1[N:17]=[C:13]([C:12]2[N:11]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH:10]=[C:9]3[C:8]=2[C:7](=[O:31])[N:6]([CH3:32])[C:5](=[O:33])[N:4]3[CH3:3])[S:14][CH:15]=1

Participants

6

Reactant 3

HCID 433294Lithium Chloride2×HCID 4311764Sodium borohydride2×HCID 86722932Ethyl 2-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thiazole-4-carboxylate

Product 1

HCID 867229335-(4-(Hydroxymethyl)thiazol-2-yl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.856 g, 22.62 mmol) was added to a solution of ethyl 2-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thiazole-4-carboxylate (step 1) (5.254 g, 11.31 mmol) and lithium chloride (0.959 g, 22.62 mmol) in ethanol (145 ml) and THF (290 ml) at 0° C. The mixture was stirred at room temperature for 16 hours. Further portions of lithium chloride (0.959 g, 22.62 mmol) and sodium borohydride (0.856 g, 22.62 mmol) were added and the mixture stirred for a further 4 hours. The reaction was quenched with saturated NaHCO3 (aq) (250 ml), diluted with water (100 ml) and extracted with chloroform (3×350 ml). The combined organic extracts were washed with water (200 ml) and brine (2×200 ml), dried over sodium sulfate and evaporated under vacuum to afford the title compound.

Workup

  1. stirringthe mixture stirred for a further 4 hours
  2. customThe reaction was quenched with saturated NaHCO3 (aq) (250 ml)
  3. additiondiluted with water (100 ml)
  4. extractionextracted with chloroform (3×350 ml)
  5. washThe combined organic extracts were washed with water (200 ml) and brine (2×200 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-b2e8b866623b46e08cb575720495bdc5
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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