Phosphorus oxychloride → methyl 2-amino-4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

HRID 2175925Notes

Reaction equation

HRID 2175925 reaction equation
P(Cl)(Cl)([Cl:3])=O.[NH2:6][C:7]1[N:8]=[C:9](O)[C:10]2[CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][C:11]=2[N:12]=1>>[NH2:6][C:7]1[N:8]=[C:9]([Cl:3])[C:10]2[CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178497331HCID 178497331, compound

Product 1

HCID 86727111methyl 2-amino-4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (16.0 mL, 172 mmol) was added to methyl 2-amino-4-hydroxy-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate (5.84 g, 27.9 mmol). The resulting mixture was heated in a sealed tube at 100° C. in the microwave for 3 hours. The solvent was evaporated. The residue was dissolved in 6 mL acetonitrile and 6 mL ice/water was added. The resulting mixture was stirred at RT for 15 minutes and purified by reverse phase preparative HPLC on a SunFire column using a gradient from 0 to 100% acetonitrile over 10 minutes (11 injections) to afford the title compound. Additional product was obtained by re-purification of mixed fractions: LC/MS (M+H)=228, 230.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in 6 mL acetonitrile
  3. addition6 mL ice/water was added
  4. custompurified by reverse phase preparative HPLC on a SunFire column
  5. customover 10 minutes

Sources & evidence

ORD record
ord-38d691caa0634eb78bcdf2bda9b8b23b
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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