Dimethylformamide → HCID 86740347, compound

HRID 867841Notes

Reaction equation

HRID 867841 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6](OC)[N:5]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([N:23]=[C:24](SC)[S:25][CH3:26])(=[O:22])=[O:21])[CH:15]=1.C[N:30](C)C=O>>[CH3:11][O:10][C:8]1[N:30]=[C:6]([CH3:7])[N:5]=[C:4]([NH:3][C:24]([S:25][CH3:26])=[N:23][S:20]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)(=[O:22])=[O:21])[N:9]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 85999525HCID 85999525, compound

Product 1

HCID 86740347HCID 86740347, compound

Procedure

To a suspension of 0.9 g of sodium hydride (50% oil dispersion) in 25 ml of dry N,N-dimethylformamide was added 2.3 g of 2-amino-4,6-dimethoxypyrimidine. The resulting yellow suspension was stirred at room temperature for 3 hrs., then added to 3.95 g of 3-pyridinylsulfonylcarbonimidodithioic acid, dimethyl ester. The reddish slurry was stirred at room temperature for 2 hours, poured into 250 g of icewater and filtered to remove 1.6 g of unreacted, carbonimidodithioic acid, dimethyl ester. The filtrate was adjusted to pH 4 by adding 10% hydrochloric acid and the precipitate was filtered off, rinsed with water until neutral and then dried invacuo to give 2.6 g of the desired compound, m.p. 146°-149° C.

Workup

  1. stirringThe reddish slurry was stirred at room temperature for 2 hours
  2. additionpoured into 250 g of icewater
  3. filtrationfiltered
  4. customto remove 1.6 g of unreacted, carbonimidodithioic acid, dimethyl ester
  5. additionby adding 10% hydrochloric acid
  6. filtrationthe precipitate was filtered off
  7. washrinsed with water until neutral and
  8. customthen dried invacuo

Sources & evidence

ORD record
ord-eff7c36a6ca9487c9536b01b2190ffb8
Source dataset
uspto-grants-1988_10
Patent number
US04776878

Reaction notes

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