Azane;hydrate → HCID 69769711, compound

HRID 1760209Notes

Reaction equation

HRID 1760209 reaction equation
[CH2:1]([N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[N:11][C:10]2[C:5]1=[N:6][C:7]([C:21]#[C:22][C:23]1([OH:27])[CH2:26][CH2:25][CH2:24]1)=[N:8][C:9]=2[Cl:20])[CH:2]=[CH2:3].O.[NH3:29]>COCCOC.[Cl-].[NH4+].C(OCC)(=O)C>[ClH:20].[CH2:1]([N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[N:11][C:10]2[C:5]1=[N:6][C:7]([CH2:21][CH2:22][C:23]1([OH:27])[CH2:26][CH2:25][CH2:24]1)=[N:8][C:9]=2[NH2:29])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 12896473Azane;hydrateHCID 22597421HCID 22597421, compound

Product 1

HCID 69769711HCID 69769711, compound

Reagents, catalysts & solvents 3

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A suspension of 1-{2-[9-allyl-6-chloro-8-(3-fluorophenyl)-9H-2-purinyl]-1-ethynyl}-1-cyclobutanol (45 g, 116.8 mmol) in 1,2-dimethoxyethane (900 ml)/conc. ammonia water (450 ml) was stirred in an autoclave at 70° C. for 5 hours. After cooling as it was, the reaction solution was diluted with an aqueous saturated ammonium chloride solution (×1) and ethyl acetate. The organic layer was washed with a saturated aqueous ammonium chloride solution (×1), dried over anhydrous sodium sulfate, and concentrated. The residue was suspended in diethyl ether, and the solid was collected by filtration and washed with diethyl ether, to give the title compound in free form (31.3 g, 98%). This free compound was suspended in 300 ml ethanol, dissolved by adding 26 ml of 5N hydrochloric acid, and concentrated. The residue was washed with diethyl ether and dried, to give 30 g of the title compound (yield 64%)

Workup

  1. temperatureAfter cooling as it
  2. washThe organic layer was washed with a saturated aqueous ammonium chloride solution (×1)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. filtrationthe solid was collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-d6e277c1c5ff4ea787727d562773ffd1
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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