Pyridine → HCID 54568578, compound

HRID 650627Notes

Reaction equation

HRID 650627 reaction equation
N1C=CC=CC=1.O1CCOCC1.[F:13][C:14]([F:47])([F:46])[C:15]1[CH:16]=[C:17]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:18][N:19]([CH3:38])[C:20]([C:22]1[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:24][C:25]([CH2:28][C:29](=O)[NH2:30])=[N:26][CH:27]=1)=[O:21]>>[F:47][C:14]([F:13])([F:46])[C:15]1[CH:16]=[C:17]([CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=1)[CH2:18][N:19]([CH3:38])[C:20]([C:22]1[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:24][C:25]([CH2:28][C:29]#[N:30])=[N:26][CH:27]=1)=[O:21]

Participants

4

Reactant 3

HCID 1049PyridineHCID 312751,4-DioxaneHCID 86757248HCID 86757248, compound

Product 1

HCID 54568578HCID 54568578, compoundYield 51%

Procedure

To a solution of 0.50 g (1.01 mmol) in 2-carbamoylmethyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide and 0.17 ml pyridine in 10 ml dioxane 0.15 ml (1.06 mmol) trifluoraceticanhydrid were added and the resulting reaction mixture was stirred for 1 hr. at 50°. The reaction mixture was poured on Ice/H2O and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 30:1) to give 0.25 g (51%) 2-cyanomethyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless solid, m.p. 114-116°.

Workup

  1. customthe resulting reaction mixture
  2. customat 50°
  3. additionThe reaction mixture was poured on Ice/H2O
  4. extractionextracted three times with 50 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 30:1)

Sources & evidence

ORD record
ord-52c62b0067c74f53b63884d7bd5001b3
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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