1,1'-Thiocarbonyldiimidazole → HCID 19864373, compound

HRID 1199958Notes

Reaction equation

HRID 1199958 reaction equation
[C:1]1([C:7]2[N:12]3[CH:13]=[N:14][C:15]([C:16]([NH2:18])=[O:17])=[C:11]3[NH:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[S:20]>O1CCCC1.[H-].[Na+]>[C:1]1([C:7]2[N:12]3[C:11]4[N:10]([C:19](=[S:20])[NH:18][C:16](=[O:17])[C:15]=4[N:14]=[CH:13]3)[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 14677483HCID 14677483, compound

Product 1

HCID 19864373HCID 19864373, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred suspension of 1.0 g of 1,2-dihydro-4-phenylimidazo[1,5-a]pyrimidine-8-carboxamide (prepared as described in Example 29) in 30 ml of dry tetrahydrofuran cooled to -78° C. in a dry ice acetone bath was added in one portion 360 mg of sodium hydride (60% dispersion in mineral oil). The reaction mixture was stirred at -78° C. for 30 minutes then 817 mg of 1,1'-thiocarbonyldiimidazole was added in one portion and the mixture was stirred at -78° C. for 3 hours then allowed to warm slowly to room temperature and was stirred at room temperature for 36 hours. The reaction mixture was quenched with water and neutralized with 5% hydrochloric acid. The aqueous solution was extracted with chloroform. The organic layer was separated and evaporated in vacuo to give the product of the example as a yellow solid, mp 316°-317° C. (dec.).

Workup

  1. stirringthe mixture was stirred at -78° C. for 3 hours
  2. temperatureto warm slowly to room temperature
  3. stirringwas stirred at room temperature for 36 hours
  4. customThe reaction mixture was quenched with water and neutralized with 5% hydrochloric acid
  5. extractionThe aqueous solution was extracted with chloroform
  6. customThe organic layer was separated
  7. customevaporated in vacuo
  8. customto give the product of the example as a yellow solid, mp 316°-317° C. (dec.)

Sources & evidence

ORD record
ord-80a1050d3a664f639fe33150db96dc1d
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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