4-Methylmorpholine → HCID 57004089, compound

HRID 248059Notes

Reaction equation

HRID 248059 reaction equation
[CH3:1][C:2]([CH3:21])([O:4][C:5](=[O:20])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:19])[C:16]([OH:18])=O)=[CH:10][CH:9]=1)[CH3:3].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:37]([N:40]1[C:47]([NH2:48])=[C:46]([NH2:49])[C:44](=[O:45])[N:43]([CH2:50][CH2:51][CH3:52])[C:41]1=[O:42])[CH2:38][CH3:39]>O1CCCC1.CN(C)C=O.C(OCC)C>[NH2:48][C:47]1[N:40]([CH2:37][CH2:38][CH3:39])[C:41](=[O:42])[N:43]([CH2:50][CH2:51][CH3:52])[C:44](=[O:45])[C:46]=1[NH:49][C:16](=[O:18])[CH:15]([CH3:19])[CH2:14][C:11]1[CH:10]=[CH:9][C:8]([S:7][CH2:6][C:5]([O:4][C:2]([CH3:1])([CH3:3])[CH3:21])=[O:20])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 19764560HCID 19764560, compound

Product 1

HCID 57004089HCID 57004089, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]thio]-alpha-methyl-benzenepropanoic acid (1.13 g, 3.64 mmol) in tetrahydrofuran (15 mL) and treat with N-methylmorpholine (0.4 mL, 3.64 mmol). Cool to -20° C. and treat with isobutyl chloroformate (0.47 mL, 3.64 mmol). Stir for 30 minutes and add a solution of 1,3-dipropyl-5,6-diaminouracil (0.82 g, 3.64 mmol) in dimethylformamide (5 mL). Stir for 3 hours at -20° C., warm to room temperature and dilute with ethyl ether (200 mL). Separate the organic phase, wash with water (200 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography to yield the title compound.

Workup

  1. stirringStir for 3 hours at -20° C.
  2. temperaturewarm to room temperature
  3. customSeparate the organic phase
  4. washwash with water (200 mL)
  5. dry with materialdry (MgSO4)
  6. customEvaporate the solvent in vacuo
  7. custompurify by flash chromatography

Sources & evidence

ORD record
ord-931db6c87e4b48aa96a3c3b1650e1d8a
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

Loading…