Methyl fluorosulfate → 1-(m-nitrophenyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1287242Notes

Reaction equation

HRID 1287242 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].S(F)(O[CH3:28])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[N:12]([CH3:28])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 9870Methyl fluorosulfateHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 127603011-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 127641771-(m-nitrophenyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione and 30 ml of dry dimethlformamide was dimethylformamide 0.6 g of about 50 % sodium hydride, and stirring was performed for 30 minutes. To this was added dropwise 2.3 g of methyl fluorosulfate and the mixture was reacted for one hour at room temperature. Then the mixture was neutralized with 5 % sodium carbonate solution and concentrated under reduced pressure to leave a residue, to which was added water to yield a crude product. This products was recrystallized from acetone to give 2.6 g of 1-(m-nitrophenyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 234°-235°C.

Workup

  1. customthe mixture was reacted for one hour at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto leave a residue
  4. customto yield a crude product
  5. customThis products was recrystallized from acetone

Sources & evidence

ORD record
ord-c675f48d77454288ac5d9311d31bd0cb
Source dataset
uspto-grants-1976_10
Patent number
US03984415

Reaction notes

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