Dimethylformamide → HCID 86651572, compound

HRID 2386243Notes

Reaction equation

HRID 2386243 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH:9]2[C:14]([NH:16][CH:17]2[CH2:19][CH2:18]2)=[O:15])[C:5](F)=[CH:4][N:3]=1.CN(C=O)C.C([O-])([O-])=O.[Cs+].[Cs+]>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:16]([CH:17]3[CH2:19][CH2:18]3)[C:14](=[O:15])[CH:9]3[CH2:10][O:11][CH2:12][CH2:13][N:8]3[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 83103480HCID 83103480, compound

Product 1

HCID 86651572HCID 86651572, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A scintillation vial equipped with a magnetic stirrer was added 4-(2-chloro-5-fluoropyrimidin-4-yl)-N-cyclopropylmorpholine-3-carboxamide (325 mg, 1.081 mmol), DMF (5 ml), Cs2CO3 (528 mg, 1.621 mmol). The reaction was stirred at 60° C. for 16 hours. The reaction solution was poured into water, extracted with ethyl acetate three times and the combined organic layers washed with sat. NaCl. The organic layers were dried with Na2SO4, filtered and dried in-vacuo to give a yellow solid. The crude material was washed with diethyl ether and filtered to afford 2-chloro-5-cyclopropyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (121 mg, 0.431 mmol, 39.9% yield) as a white solid. MS [M+H] found 281.

Workup

  1. customA scintillation vial equipped with a magnetic stirrer
  2. extractionextracted with ethyl acetate three times
  3. washthe combined organic layers washed with sat. NaCl
  4. dry with materialThe organic layers were dried with Na2SO4
  5. filtrationfiltered
  6. customdried in-vacuo
  7. customto give a yellow solid
  8. washThe crude material was washed with diethyl ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8a4a7c9955634637ac2a5837a129ca4d
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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