Morpholine → HCID 58382522, compound

HRID 1027476Notes

Reaction equation

HRID 1027476 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][C:15]1[N:16]=[C:17]([O:29][CH2:30][CH2:31][CH3:32])[C:18]2[N:23]=[C:22]([C:24]3[O:25][CH:26]=[CH:27][CH:28]=3)[O:21][C:19]=2[N:20]=1.[Br:33][C:34]1[O:38][C:37]([C:39]2[O:40][C:41]3[N:42]=[C:43]([CH2:52]Br)[N:44]=[C:45]([O:48][CH2:49][CH2:50][CH3:51])[C:46]=3[N:47]=2)=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)(=O)C.O>[Br:33][C:34]1[O:38][C:37]([C:39]2[O:40][C:41]3[N:42]=[C:43]([CH2:52][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[N:44]=[C:45]([O:48][CH2:49][CH2:50][CH3:51])[C:46]=3[N:47]=2)=[CH:36][CH:35]=1.[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:22]1[O:21][C:19]2[N:20]=[C:15]([CH2:14][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:16]=[C:17]([O:29][CH2:30][CH2:31][CH3:32])[C:18]=2[N:23]=1

Participants

9

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67175825HCID 67175825, compoundHCID 67175878HCID 67175878, compound

Product 2

HCID 58382522HCID 58382522, compoundHCID 58382524HCID 58382524, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

91.5 mg of morpholine and 207 mg of potassium carbonate were added to a solution of 169 mg of the mixture of 5-bromomethyl-2-furan-2-yl-7-propoxy-oxazolo[5,4-d]pyrimidine and 2-(5-bromo-furan-2-yl)-5-bromomethyl-7-propoxy-oxazolo[5,4-d]pyrimidine obtained in step (a) in 3 ml of dimethylformamide. The reaction mixture was stirred at room temperature for 48 h. Then 50 ml each of water and ethyl acetate were added, the mixture was filtered through a Varian ChemElut cartridge, the cartridge washed with 10 ml of ethyl acetate, and the combined filtrates were evaporated to dryness in vacuo. Preparative HPLC (method HPLC1) of the residue yielded 41 mg of 2-(5-bromo-furan-2-yl)-5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidine (example 3) and 25 mg of the title compound in the form of 2-furan-2-yl-5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidine trifluoroacetic acid salt.

Workup

  1. filtrationthe mixture was filtered through a Varian ChemElut cartridge
  2. washthe cartridge washed with 10 ml of ethyl acetate
  3. customthe combined filtrates were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-1a1c3a51a45e48c4934be435e9fae2f9
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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