Sodium borohydride → HCID 18789140, compound

HRID 1106534Notes

Reaction equation

[C:1]([N:5]1[C:13]2[N:12]3[N:14]=[CH:15][CH:16]=[C:11]3[N:10]=[C:9](Cl)[C:8]=2[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1.CO.[Pd](Cl)Cl>[C:1]([N:5]1[C:13]2[N:12]3[N:14]=[CH:15][CH:16]=[C:11]3[N:10]=[CH:9][C:8]=2[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

In a mixed solvent of 300 ml of tetrahydrofuran and 150 ml of methanol were dissolved 11.30 g of 8-tert-butyl-5-chloro-6,7-dihydro-8H-pyrrolo[3,2-e]pyrazolo-[1,5-a]pyrimidine, and the reaction system was cooled to 0° C. To the solution were gradually added 3.75 g of palladium chloride and 7.83 g of sodium borohydride, and the mixture was stirred for 30 minutes at 0° C. Furthermore, 7.50 g of palladium chloride and 5.66 g of sodium borohydride were gradually added, and the resultant mixture was stirred for 30 minutes at 0° C. and for 2 hours at room temperature. The reaction solvent was distilled off under reduced pressure, and the resultant crude product was subjected to column chromatography on silica gel (ethyl acetate→ethyl acetate:methanol=10:1) to obtain 3.94 g (yield: 40.4%) of the intended product.

Workup

distillationThe reaction solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-a72c5f83543e4b038a9194bee8e36eda
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057330

Reaction notes

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