Pyridine → HCID 178462380, compound

HRID 60532Notes

Reaction equation

HRID 60532 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[N:13]=[C:12]([S:14][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[N:11]=[C:10]([OH:23])[CH:9]=1.[C:24]([S-:26])#[N:25].[K+].BrBr>CN(C=O)C.O>[NH2:25][C:24]1[S:26][C:9]2[C:10]([OH:23])=[N:11][C:12]([S:14][C@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])=[N:13][C:8]=2[N:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 178462378HCID 178462378, compound

Product 1

HCID 178462380HCID 178462380, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Pyridine (0.6 g, 7.6 mmol) was added to 6-amino-2-{[(1S)-1-phenylethyl]thio}pyrimidin-4-ol (1 g, 4 mmol) and KSCN (1.7 g, 16 mmol) in DMF (20 mL). The reaction mixture was cooled to 0° C. and bromine (0.65 g, 4.0 mmol) was then added in one portion. The reaction mixture was poured into water after 2 h and the orange precipitate was filtered off and washed with water. The solid was suspended in a mixture of DMF (6 mL) and water (2 mL) and heated to 110° C. After 30 h, the reaction mixture was poured into water, the yellowish precipitate was filtered off and washed with water and ether. The solid was dried in vacuum at 40° C. to give the title compound (0.8 g, 65% yield).

Workup

  1. filtrationthe orange precipitate was filtered off
  2. washwashed with water
  3. additionThe solid was suspended in a mixture of DMF (6 mL) and water (2 mL)
  4. temperatureheated to 110° C
  5. additionthe reaction mixture was poured into water
  6. filtrationthe yellowish precipitate was filtered off
  7. washwashed with water and ether
  8. customThe solid was dried in vacuum at 40° C.

Sources & evidence

ORD record
ord-10b36c70d66c4fb7856cfa894c7a9c08
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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