Ammonia → HCID 131736062, compound

HRID 1050335Notes

Reaction equation

HRID 1050335 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH:19]1[CH2:21][CH2:20]1)[N:6]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16].[NH3:22]>C(O)C>[CH:19]1([C:5]2[N:6]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:7]3[C:3]([N:4]=2)=[C:2]([NH2:22])[N:10]=[CH:9][N:8]=3)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131736063HCID 131736063, compound

Product 1

HCID 131736062HCID 131736062, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube a stirred suspension of 2-[(6-chloro-8-cyclopropyl-purin-9-yl)methoxy]ethyl-trimethyl-silane (5, 0.8 g, 2.46 mmol) and 30% aqueous ammonia (10 mL) in ethanol (10 mL) was heated at 120° C. for 14 h. After TLC showed consumption of 5, ethanol was removed under reduced pressure and the residue was washed with water (10 mL) and diethyl ether (10 mL) to obtain 8-cyclopropyl-9-(2-trimethylsilylethoxymethyl)purin-6-amine (6) as a white solid. Yield: 703 mg, 93%; MS (ESI) m/z 306.30 [M+1]+; 1H NMR (400 MHz, CDCl3) δ 8.00 (s, 1H), 7.10 (s, 2H), 5.64 (s, 2H), 3.57 (m, 2H), 2.24 (m, 1H), 1.08 (m, 4H), 0.83 (m, 2H), 0.09 (s, 9H).

Workup

  1. customconsumption of 5, ethanol
  2. customwas removed under reduced pressure
  3. washthe residue was washed with water (10 mL) and diethyl ether (10 mL)

Sources & evidence

ORD record
ord-9e8d208acd184bf7b7990f1fcc8c7e3a
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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