Borane → HCID 19087700, compound

HRID 1464271Notes

Reaction equation

HRID 1464271 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[NH:9][C:8]1=[O:18])(O)=[O:2].B>O1CCCC1>[OH:2][CH2:1][CH2:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[NH:9][C:8]1=[O:18]

Participants

4

Reactant 2

HCID 6331BoraneHCID 19087746HCID 19087746, compound

Product 1

HCID 19087700HCID 19087700, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 1-(3-carboxypropyl)-2,4(1H,3H)-quinazolinedione (2.00 g) in tetrahydrofuran (40 ml) was added 1M borane in tetrahydrofuran (24.2 ml) on an ice-bath, and the mixture was stirred for additional 2 hours at room temperature. The reaction mixture was quenched with 1N hydrochloric acid, and the organic solvent was evaporated. The residue was triturated with water, filtered and washed in turn with water and ethyl ether to give 1-(4-hydroxybutyl)-2,4(1H,3H)-quinazolinedione (1.74 g) as a crystal.

Workup

  1. customThe reaction mixture was quenched with 1N hydrochloric acid
  2. customthe organic solvent was evaporated
  3. customThe residue was triturated with water
  4. filtrationfiltered
  5. washwashed in turn with water and ethyl ether

Sources & evidence

ORD record
ord-3363c7c55131426982dd89bfc1fbe724
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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