4-chloro-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-amine → 4-Methoxy-1,5,6,7-tetrahydro-2H-cyclopenta[d]pyrimidin-2-imine

HRID 1744968Notes

Reaction equation

HRID 1744968 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[N:5]=[C:4]([NH2:11])[N:3]=1.[CH3:12][O-:13].[Na+]>C1(C)C(C)=CC=CC=1.CO>[CH3:12][O:13][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[N:5]=[C:4]([NH2:11])[N:3]=1

Participants

5

Reactant 2

HCID 2303324-chloro-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-amineHCID 10942334Sodium Methoxide

Product 1

HCID 2307444-Methoxy-1,5,6,7-tetrahydro-2H-cyclopenta[d]pyrimidin-2-imineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent

Procedure

(S M:Ross, L. O.; Goodman, L.; Baker, B. R. J. Am. Chem. Soc. 1959, 81, 3108) 5.3 grams of 4-chloro-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamine was dissolved in 200 ml xylene and 30 ml absolute methanol. Then 5.4 gram for sodium methoxide was added and the mixture was refluxed for 3 hours. Then the solvent was removed in vacuo and 100 ml water was added to the residue. Filter and wash the cake with water (50 ml). The solid was further vacuumed to dry for several hours. The desired product weighed 4.8 gram (98% yield). Mp: 133.8˜134.9° C.; MS: 166.2.0 (M+H)

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThen the solvent was removed in vacuo and 100 ml water
  3. additionwas added to the residue
  4. filtrationFilter
  5. washwash the cake with water (50 ml)
  6. customto dry for several hours

Sources & evidence

ORD record
ord-796776ba14fe496296c07281373db770
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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