Water → HCID 21846220, compound

HRID 619303Notes

Reaction equation

HRID 619303 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](F)=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1.[CH3:22][S-:23].[Na+].C[S-].O>CS(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([S:23][CH3:22])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1969684-(4-Fluoro-1-naphthalenyl)-6-(1-methylethyl)-2-pyrimidinamineHCID 519392MercaptomethanideHCID 4378561Sodium methanethiolate

Product 1

HCID 21846220HCID 21846220, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Amino-4-(4-fluoronaphth-1-yl)-6-isopropyl-pyrimidine (0.281 g) was dissolved in dimethyl sulphoxide (DMSO) (10 mL) and sodium thiomethoxide (0.070 g) was added. The reaction mixture was stirred at room temperature for 2 hours at which time another equivalent of thiomethoxide was added and the reaction stirred for another 2 hours. The mixture was poured into water (100 mL) and the product was extracted into ethyl acetate/hexane (3×50 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The reaction product was purified by column chromatography on silica gel, eluting with hexane/ethyl acetate to give 2-amino-4-(4-methylthionaphth-1-yl)-6-isopropylpyrimidine (0.303 g), m.p. 139-140° C.

Workup

  1. additionwas added
  2. extractionthe product was extracted into ethyl acetate/hexane (3×50 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe reaction product was purified by column chromatography on silica gel
  6. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a93f5369300e4464b74d9031621d98c7
Source dataset
uspto-grants-1999_09
Patent number
US05958934

Reaction notes

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