Hydrochloric Acid → Ammonium Acetate

HRID 731530Notes

Reaction equation

HRID 731530 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:12]=[C:13]([NH:22][C:23]([CH3:28])([CH2:26][OH:27])[CH2:24][OH:25])[C:14]2[S:19][C:18]([O:20]C)=[N:17][C:15]=2[N:16]=1.Cl.[OH2:30]>O1CCOCC1>[C:26]([O-:27])(=[O:30])[CH3:23].[NH4+:12].[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:12]=[C:13]([NH:22][C:23]([CH2:26][OH:27])([CH3:28])[CH2:24][OH:25])[C:14]2[S:19][C:18](=[O:20])[NH:17][C:15]=2[N:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 690604962-[[5-[[(2,3-Difluorophenyl)methyl]thio]-2-methoxythiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediol

Product 2

HCID 517165Ammonium AcetateYield 0.1%HCID 117425175-[[(2,3-Difluorophenyl)methyl]thio]-7-[[2-hydroxy-1-(hydroxymethyl)-1-methylethyl]amino]-thiazolo[4,5-d]pyrimidin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product from step (g) (0.3 g) was suspended in a mixture of dioxan (50 ml) and conc.HCl (1 ml). Water (1 ml) was added and the resultant solution heated at 60° C. for 12 hours. Allowed to stand over weekend. Solvents removed in vacuo and residue taken up in water. Yellow precipitate collected by filtration and washed with water. Purified using prep. Hplc Acetonitrile: 0.1% ammonium acetate (90:10 to 95:5) over 25 minutes to give 0.063 g of the desired product. 22% yield.

Workup

  1. waitAllowed to stand over weekend
  2. customSolvents removed in vacuo and residue
  3. filtrationYellow precipitate collected by filtration
  4. washwashed with water
  5. customPurified

Sources & evidence

ORD record
ord-2ec21248001442dd86fe37ff21149857
Source dataset
uspto-grants-2009_09
Patent number
US07585867B2

Reaction notes

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