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Hydrochloric Acid → 6-Amino-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-one

HRID 1011186
Notes
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Reaction equation

HRID 1011186 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[C:12]([O:23]C)[N:13]3[CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:9]([NH2:25])[N:8]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>CO.O1CCOCC1.O>[NH2:25][C:9]1[N:8]=[C:7]([O:6][CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:23])[N:13]2[CH2:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576997352-[(2-Cyclopropylethyl)oxy]-8-(methyloxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

Product 1

HCID 576997106-Amino-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-oneYield 77.8%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
2×
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Procedure

2-[(2-Cyclopropylethyl)oxy]-8-(methoxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (0.1259 g) was dissolved in methanol (5 mL) and added 4N hydrogen chloride in 1,4-dioxane (2 mL). The reaction was stirred at room temperature for 4 hours. The reaction mixture was evaporated under reduced pressure to give a solid which was then suspended in water (1 mL) and small quantity of methanol (2-3 mL). This was then neutralised (to pH 7) by the addition of 2N sodium hydroxide. The suspension was evaporated to near dryness under reduced pressure and then suspended the solid in water (3 mL). The solid was filtered off under suction and washed with a few drops of methanol before being air-dried under suction. This material was then dried to constant weight under vacuo at 50° C. to give the title compound (94 mg).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto give a solid which
  3. customThe suspension was evaporated
  4. filtrationThe solid was filtered off under suction
  5. washwashed with a few drops of methanol
  6. custombefore being air-dried under suction
  7. customThis material was then dried to constant weight under vacuo at 50° C.

Sources & evidence

ORD record
ord-da2d59cc97ee47018348c530fe9111c8
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977344B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes