Triethylamine → HCID 86651565, compound

HRID 2386223Notes

Reaction equation

HRID 2386223 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH2:9])=[C:4]([Cl:10])[N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH:12]1[C:17](O)=[O:18].C(N(CC)CC)C>C(O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([Cl:10])[C:5]2[NH:9][C:17](=[O:18])[CH:12]3[CH2:13][O:14][CH2:15][CH2:16][N:11]3[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 33401523-Morpholinecarboxylic acidHCID 133921552,4,6-Trichloropyrimidin-5-amine

Product 1

HCID 86651565HCID 86651565, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A round-bottom flask was charged with 2,4,6-trichloropyrimidin-5-amine (982 mg, 4.95 mmol), morpholine-3-carboxylic acid (649 mg, 4.95 mmol) and triethylamine (2.78 mL, 19.79 mmol) in ethanol (20 mL). The mixture was heated at 75° C. for 3 days then diluted with water and extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered and dried in vacuo to give 500 mg of crude 2,4-dichloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one which was used without further purification. MS [M+H] Found 275.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8a57b2a5a36a4a06b040829aaa0f809e
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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