Water → HCID 86651595, compound

HRID 2386277Notes

Reaction equation

HRID 2386277 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]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].C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:9]([CH:10]3[CH2:15][CH2:14][S:13][CH2:12][CH2:11]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 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 45790954Morpholine-3-carboxylic acid hydrochlorideHCID 86651594HCID 86651594, compound

Product 1

HCID 86651595HCID 86651595, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 2,4-dichloro-N-(tetrahydro-2H-thiopyran-4-yl)pyrimidin-5-amine (864 mg, 3.27 mmol) and morpholine-3-carboxylic acid hydrochloride (822 mg, 4.91 mmol) in DMSO (15 ml) was added diisopropylethylamine (2.29 ml, 13.1 mmol), and the reaction mixture was stirred at 95° C. for 4 hours. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. The solid was chromatographed by silica gel (hexane/ethyl acetate, 19:1 to 3:2) to afford partially purified 2-chloro-5-(tetrahydro-2H-thiopyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (83.6 mg, 0.245 mmol, 7.5% yield) as a white solid. MS [M+H] found 341.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude solid
  6. customThe solid was chromatographed by silica gel (hexane/ethyl acetate, 19:1 to 3:2)

Sources & evidence

ORD record
ord-27c5a6f918c145d6b3ecd8c2f317c078
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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