Sodium hydride → 5-benzyl-4-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-amine

HRID 1805866Notes

Reaction equation

HRID 1805866 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[SH:12].[CH2:13]([N:20]1[C:28]2[C:27](Cl)=[N:26][C:25]([NH2:30])=[N:24][C:23]=2[CH:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN1C(=O)CCC1.O>[CH2:13]([N:20]1[C:28]2[C:27]([S:12][C:5]3[C:6]([CH3:11])=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=3[CH3:3])=[N:26][C:25]([NH2:30])=[N:24][C:23]=2[CH:22]=[CH:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2844492,4,6-TrimethylthiophenolHCID 576936175-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine

Product 1

HCID 576935835-benzyl-4-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-amineYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a stirred suspension of NaH (48 mg, 2 mmol) in dry NMP (2 mL) was added 2,4,6-trimethyl-benzene-1-thiol (191 mg, 1.2 mmol) The mixture was and stirred at room temperature for 30 min under argon. The reaction mixture was then added to a solution of 5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine (103 mg, 0.4 mmol) in dry NMP (2.5 mL) and heated at 60° C. for 16 h. After completion of the reaction, the resulting mixture was diluted with water and washed with EtOAc. The combined organic layers were washed with water, 2% NaOH, and brine; dried over Na2SO4; filtered; and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (2:1-1:3) to give the product as a light yellow solid (131 mg, 88%).

Workup

  1. temperatureheated at 60° C. for 16 h
  2. customAfter completion of the reaction
  3. washwashed with EtOAc
  4. washThe combined organic layers were washed with water, 2% NaOH, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationand concentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with hexanes/ethyl acetate (2:1-1:3)

Sources & evidence

ORD record
ord-4b6452abe54b44128ca13d3e7cb8d52d
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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