Water → 4-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid amide

HRID 873549Notes

Reaction equation

HRID 873549 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]([OH:29])=O)[N:22]=2)=[C:17]([CH3:30])[C:16]=1[CH:31]1[C:44]2[C:43](=[O:45])[CH2:42][C:41]([CH3:47])([CH3:46])[CH2:40][C:39]=2[O:38][C:37]2[CH2:36][C:35]([CH3:49])([CH3:48])[CH2:34][C:33](=[O:50])[C:32]1=2.O.N.O>C1COCC1.CN(C=O)C.C(OCC)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]([NH2:3])=[O:29])[N:22]=2)=[C:17]([CH3:30])[C:16]=1[CH:31]1[C:32]2[C:33](=[O:50])[CH2:34][C:35]([CH3:48])([CH3:49])[CH2:36][C:37]=2[O:38][C:39]2[CH2:40][C:41]([CH3:47])([CH3:46])[CH2:42][C:43](=[O:45])[C:44]1=2

Participants

8

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 12896473Azane;hydrateHCID 1177005224-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid

Product 1

HCID 1177007744-[4-Methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid amideYield 86%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (50.1 mg, 0.309 mol) was added to a solution of the 4-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylic acid obtained in Example 75-4 (133 mg, 0.257 mmol) in THF (2.0 mL) and DMF (0.5 mL) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 30 minutes. Thereafter, 27% ammonia water was added to the resulting solution, and the mixture thus obtained was further stirred at the same temperature as above for 30 minutes. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate twice. The organic layer thus obtained was washed with 1 M-hydrochloric acid and brine, and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The residue thus obtained was solidified with diethyl ether to obtain the title compound (114 mg, yield: 86%).

Workup

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringwas further stirred at the same temperature as above for 30 minutes
  4. extractionthe mixed solution was then extracted with ethyl acetate twice
  5. customThe organic layer thus obtained
  6. washwas washed with 1 M-hydrochloric acid and brine
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. distillationAfter that, the solvent was distilled away under reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-3968d3e88ecd40b0a05d18ea2740eb39
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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