2,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidine → 4-Chloro-2-(methylsulfanyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 1508944Notes

Reaction equation

HRID 1508944 reaction equation
Cl[C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[CH3:12][S-:13].[Na+]>C1COCC1.C(=O)(O)[O-].[Na+]>[Cl:11][C:4]1[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=[C:2]([S:13][CH3:12])[N:3]=1

Participants

5

Reactant 2

HCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 2316404-Chloro-2-(methylsulfanyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidineYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.250 g, 1.32 mmol) and sodium thiomethoxide (0.093 g, 1.32 mmol) in THF (10 mL) was stirred at rt for 6 h. After this time, the mixture was diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.210 g, 84%) as an off-white solid. MW=200.69. 1H NMR (DMSO-d6, 300 MHz) δ 2.90 (t, J=7.6 Hz, 2H), 2.71 (t, J=7.6 Hz, 2H), 2.56 (s, 3H), 2.10 (quin, J=7.6 Hz, 2H); APCI MS m/z 201 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7f703e3252bc4d5885ae99ac1ea31d92
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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