Diisopropylethylamine → HCID 86651603, compound

HRID 1696048Notes

Reaction equation

HRID 1696048 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH2:10][CH:11]2[CH2:15][CH2:14][O:13][CH2:12]2)=[CH:4][N:3]=1.Cl.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH:18]1[C:23](O)=[O:24].CCN(C(C)C)C(C)C>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:9]([CH2:10][CH:11]3[CH2:15][CH2:14][O:13][CH2:12]3)[C:23](=[O:24])[CH:18]3[CH2:19][O:20][CH2:21][CH2:22][N:17]3[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 45790954Morpholine-3-carboxylic acid hydrochlorideHCID 86651602HCID 86651602, compound

Product 1

HCID 86651603HCID 86651603, compoundYield 408.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Dichloro-N-((tetrahydrofuran-3-yl)methyl)pyrimidin-5-amine (7 g, 28.2 mmol), morpholine-3-carboxylic acid hydrochloride (832 mg, 4.97 mmol), and DIPEA (2.67 ml, 15.28 mmol) were combined in DMSO (8 ml). The reaction mixture was heated overnight at 100° C. Upon cooling the solution was diluted with water then extracted twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 6.6 g of 2-chloro-5-((tetrahydrofuran-3-yl)methyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a brown oil which was used without further purification. [M+H] found 325.

Workup

  1. temperatureUpon cooling the solution
  2. extractionthen extracted twice with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-98ca3c31231d4da59023def1937f6523
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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