Pyridine → HCID 178462381, compound

HRID 415363Notes

Reaction equation

HRID 415363 reaction equation
[C:1]([S-:3])#[N:2].[K+].N1C=CC=CC=1.[NH2:11][C:12]1[N:17]=[C:16]([S:18][C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH3:20])[N:15]=[C:14]([OH:28])[CH:13]=1.BrBr>CN(C=O)C.O>[NH2:2][C:1]1[S:3][C:13]2[C:14]([OH:28])=[N:15][C:16]([S:18][C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[CH3:20])=[N:17][C:12]=2[N:11]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 178462379HCID 178462379, compound

Product 1

HCID 178462381HCID 178462381, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

KSCN (10.76 g, 110.7 mmol) and pyridine (3.9 mL, 49.2 mmol) was added to 6-amino-2-{[(1S)-1-(2-fluorophenyl)ethyl]thio}pyrimidin-4-ol (6.53 g, 24.6 mmol) in DMF (70 mL). The mixture was cooled to 0° C. and Br2 was added dropwise. After 3.5 h the reaction mixture was poured into water and the formed precipitate was collected by filtration. The solid was suspended in a mixture of DMF (75 mL) and water (15 mL) and heated to 120° C. for 8 h. The reaction mixture was poured into water and the solid was collected by filtration and dried in vacuo at 40° C. to give the title compound (6.42 g, 81% yield).

Workup

  1. filtrationthe formed precipitate was collected by filtration
  2. additionThe solid was suspended in a mixture of DMF (75 mL) and water (15 mL)
  3. temperatureheated to 120° C. for 8 h
  4. additionThe reaction mixture was poured into water
  5. filtrationthe solid was collected by filtration
  6. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-dd48bad7186e444e8532d80ebd29139c
Source dataset
uspto-grants-2012_01
Patent number
US08088780B2

Reaction notes

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