Ammonia → 2-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1011013Notes

Reaction equation

HRID 1011013 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4](Cl)[N:3]=1.[NH3:19]>CC(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([NH2:19])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 576997032,6-Dichloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine

Product 1

HCID 576998042-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,6-dichloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine (3.08 g, containing triphenylphosphine oxide) was heated with 2M ammonia in IPA (50 mL) at 50° C., overnight. The reaction mixture was then evaporated to dryness to give a yellow solid. This material (3.2089 g) was recrystallised using methanol (50 mL) and after cooling the resultant solid was filtered and washed with methanol (5 mL) to give the title compound (1.5554 g). The filtrate was evaporated and recrystallised from methanol (25 mL) and after cooling the resultant solid was filtered to give a second crop (0.2324 g) and was consistent with first batch by NMR and LCMS.

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customto give a yellow solid
  3. customThis material (3.2089 g) was recrystallised
  4. temperatureafter cooling the resultant solid
  5. filtrationwas filtered
  6. washwashed with methanol (5 mL)

Sources & evidence

ORD record
ord-bad6482d8b25469683fd20bb289c6f78
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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