Sodium Acetate → methyl 4-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-6-yl)benzoate

HRID 590622Notes

Reaction equation

HRID 590622 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.C([O-])(=O)C.[Na+].Br[CH2:16][C:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=O>O.CO>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]2[CH:16]=[C:17]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[NH:9][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 13612771Methyl 4-(2-bromoacetyl)benzoateHCID 178507952HCID 178507952, compound

Product 1

HCID 178497455methyl 4-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-6-yl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2,6-diamino-4-hydroxypyrimidine (CAS: 56-06-4, 1 g, 7.93 mmol) and sodium acetate (0.85 g, 10.32 mmol) in water (180 mL) was stirred at 100° C. for 30 minutes. Methyl 4-(2-bromoacetyl)benzoate (2.24 g, 8.72 mmol) was suspended in MeOH (25 mL) and was added slowly to the above solution. The reaction mixture was then stirred at 100° C. for 16-20 h and then cooled to room temperature. The residue was filtered and dried. It was then stirred in CH2Cl2 (10 mL) and filtered to provide XI-8-I (1.07 g, 47.5%). LCMS: m/z 285 (M+1)+.

Workup

  1. additionwas added slowly to the above solution
  2. temperaturecooled to room temperature
  3. filtrationThe residue was filtered
  4. customdried
  5. stirringIt was then stirred in CH2Cl2 (10 mL)
  6. filtrationfiltered
  7. customto provide XI-8-I (1.07 g, 47.5%)

Sources & evidence

ORD record
ord-703ecf938d9e4e6e9c0f5c3874ceb07c
Source dataset
uspto-grants-2016_01
Patent number
US09233983B2

Reaction notes

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