4-Methylmorpholine → HCID 178498437, compound

HRID 1957567Notes

Reaction equation

HRID 1957567 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([OH:22])[C:5]2[CH2:11][CH:10]([CH2:12][CH2:13][C:14]3[S:18][C:17]([C:19]([OH:21])=O)=[CH:16][CH:15]=3)[CH2:9][NH:8][C:6]=2[N:7]=1.CN1CCOCC1.ClC1N=C(OC)N=C(OC)N=1.[C:41]([CH:45]1[CH2:49][CH2:48][NH:47][CH2:46]1)([O:43][CH3:44])=[O:42]>CN(C)C=O>[NH2:1][C:2]1[N:3]=[C:4]([OH:22])[C:5]2[CH2:11][CH:10]([CH2:12][CH2:13][C:14]3[S:18][C:17]([C:19]([N:47]4[CH2:48][CH2:49][CH:45]([C:41]([O:43][CH3:44])=[O:42])[CH2:46]4)=[O:21])=[CH:16][CH:15]=3)[CH2:9][NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 4114360Methyl Pyrrolidine-3-carboxylateHCID 178508889HCID 178508889, compound

Product 1

HCID 178498437HCID 178498437, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a sample of 150 mg (0.47 mmol) of 5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarboxylic acid in a three-necked round bottomed flask under an atmosphere of nitrogen were added 3.6 mL anhydrous dimethylformamide and 0.11 mL (0.99 mmol) of N-methylmorpholine. The reaction mixture was stirred and 90 mg (0.51 mmol) of 2-chloro-4,6-dimethoxy-1,3,5-triazine were added at once. The reaction mixture was stirred at room temperature for 0.5 hours and 162 mg (1.25 mmol) of 3-carbomethoxypyrrolidine were added in 1.0 mL of dimethylformamide. After stirring at room temperature for another 3.5 hours, the reaction was concentrated in vacuo and the residue was chromatographed on silica gel with 2-8% CH3OH/CHCl3 to give 78 mg (40%) of methyl 1-{5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarbonyl}pyrrolidine-3-carboxylate as a white solid. Mass Spectrum (FAB+): M+1=432; IR (KBr, cm-1): 643, 734, 768, 809, 1219, 1336, 1417, 1464, 1601, 1684, 1736, 2854, 2924, 3390; UV (C2H5 OH): λmax =222 (ε=21034), 279 (ε=19777).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 0.5 hours
  2. stirringAfter stirring at room temperature for another 3.5 hours
  3. concentrationthe reaction was concentrated in vacuo
  4. customthe residue was chromatographed on silica gel with 2-8% CH3OH/CHCl3

Sources & evidence

ORD record
ord-b962160eaf154a6eb5da8cf777296700
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

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