Methanol → HCID 59803663, compound

HRID 1666218Notes

Reaction equation

HRID 1666218 reaction equation
C(OC[N:9]1[C:17]2[N:16]=[C:15]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[N:14]([CH3:30])[C:13]=2[C:12](=[O:31])[N:11]([CH2:32][C:33]#[CH:34])[C:10]1=[O:35])(=O)C(C)(C)C.O1CCCC1.CO.O.[OH-].[Li+]>ClCCl.CO>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([C:19]#[C:18][C:15]2[N:14]([CH3:30])[C:13]3[C:12](=[O:31])[N:11]([CH2:32][C:33]#[CH:34])[C:10](=[O:35])[NH:9][C:17]=3[N:16]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59803681HCID 59803681, compound

Product 1

HCID 59803663HCID 59803663, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of {8-[(3,4-dimethoxyphenyl)ethynyl]-7-methyl-2,6-dioxo-1-prop-2-ynyl-1,2,6,7-tetrahydro-3H-purin-3-yl}methyl pivalate (471 mg, 0.98 mmol) in a 4:1 mixture of dry tetrahydrofurane and methanol (20 mL) was added lithium hydroxide monohydrate (127 mg, 1.63 mmol). The mixture was stirred at room temperature for 3 h (TLC-control: dichloromethane/methanol, 9.5:0.5, Rf=0.40 for the product). Subsequently the solvent was removed under reduced pressure, the remaining residue was dissolved in water (30 mL) and acidified with diluted hydrochloric acid. The precipitate was filtered under reduced pressure, washed with water and dried at 70° C., yielding 334 mg (93 yield for the deprotection reaction) of the title compound.

Workup

  1. customSubsequently the solvent was removed under reduced pressure
  2. dissolutionthe remaining residue was dissolved in water (30 mL)
  3. filtrationThe precipitate was filtered under reduced pressure
  4. washwashed with water
  5. customdried at 70° C.
  6. customyielding 334 mg (93

Sources & evidence

ORD record
ord-766d73ec614e43dc96e2489c79c878bc
Source dataset
uspto-grants-2011_10
Patent number
US08044061B2

Reaction notes

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