HCID 15754624, compound → HCID 59679895, compound

HRID 1924106Notes

Reaction equation

HRID 1924106 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]2[CH:18]=1)([O-])=O>CO>[N:11]1[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])=[CH:18][N:13]2[CH:14]=[CH:15][CH:16]=[N:17][C:12]=12

Participants

3

Reactant 1

HCID 15754624HCID 15754624, compound

Product 1

HCID 59679895HCID 59679895, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Nitro-phenyl)-imidazo[1,2-a]pyrimidine (2 g, 8.33 mmol) and NaHS (2.8 g, 6 eq) were refluxed in 25% aqueous methanol (40 ml) water overnight. The reaction mixture was cooled to room temperature, and concentrated to dryness. Methanol (10 ml) and water (30 ml) were added, and the product was extracted with CH2Cl2 (3×100 ml). The combined organic layers were concentrated to dryness, chased with 10% MeOH:CH2Cl2 and dried under high vacuum at 45° C. to obtain the product as an orange solid (1.34 g, 76% yield). (MS, M++H=211.1)

Workup

  1. concentrationconcentrated to dryness
  2. additionMethanol (10 ml) and water (30 ml) were added
  3. extractionthe product was extracted with CH2Cl2 (3×100 ml)
  4. concentrationThe combined organic layers were concentrated to dryness
  5. dry with materialCH2Cl2 and dried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-e5ae95127f054a4fa74b2cbc33095141
Source dataset
uspto-grants-2012_05
Patent number
US08178536B2

Reaction notes

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