1-Butanol → HCID 58757226, compound

HRID 386412Notes

Reaction equation

HRID 386412 reaction equation
[CH2:1]([N:8]1[C:16](Br)=[N:15][C:14]2[C:9]1=[N:10][C:11]([Cl:19])=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:24])CCC>Cl>[NH2:18][C:13]1[N:12]=[C:11]([Cl:19])[N:10]=[C:9]2[C:14]=1[NH:15][C:16](=[O:24])[N:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2631-ButanolHCID 59127749HCID 59127749, compound

Product 1

HCID 58757226HCID 58757226, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The product from Step 3 (2 g, 5.9 mmol) was suspended in 12 N HCl (35 mL) and n-butanol (35 mL) and the mixture heated at 100° C. for 7 h and then allowed to cool to room temperature. The reaction mixture was evaporated to dryness in vacuo, and then partitioned between 2 N NaOH (50 mL) and dichloromethane (50 mL). The organic layer was separated and found to contain some unreacted starting material only and was discarded, while the aqueous layer was neutralized with concentrated HCl and the resulting precipitate collected by filtration and washed with ethyl acetate to give 6-amino-9-benzyl-2-chloro-7,9-dihydro-purin-8-one as an off-white solid (1.5 g, 94%) which was found to be >90% pure and was used with no further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. custompartitioned between 2 N NaOH (50 mL) and dichloromethane (50 mL)
  3. customThe organic layer was separated
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-fe41fd5d7ab64e3fac78ad4051b1dbc3
Source dataset
uspto-grants-2013_02
Patent number
US08372836B2

Reaction notes

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