Hydrochloric Acid → HCID 58338026, compound

HRID 1409295Notes

Reaction equation

HRID 1409295 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].Cl[C:15]1[C:16]2[N:23]=[CH:22][S:21][C:17]=2[N:18]=[CH:19][N:20]=1.CCN(CC)CC.Cl>CN(C=O)C.O>[CH3:13][C:7]1[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][NH:2][C:15]1[C:16]2[N:23]=[CH:22][S:21][C:17]=2[N:18]=[CH:19][N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2630077-Chlorothiazolo[5,4-D]pyrimidineHCID 67032195HCID 67032195, compound

Product 1

HCID 58338026HCID 58338026, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(2-Aminoethoxy)-3-methylphenol hydrochloride (0.30 g, 1.5 mmol), 7-chlorothiazolo[5,4-d]pyrimidine (0.25 g, 1.5 mmol), and Et3N (300 mg, 3 mmol) were dissolved with magnetic stirring in DMF (6 mL) in a 25 mL round bottom flask equipped with a dry nitrogen line at 25° C. After 24 h, the reaction mixture was diluted with H2O (120 mL), and treated with 2 N HCl to adjust the pH to 5. After 24 h, a dark yellow solid precipitated and was removed by filtration. The filtrate was extracted with EtOAc (2×50 mL), and the pooled organic fractions were filtered and concentrated in vacuo to afford 3-methyl-4-[2-(thiazolo[5,4-d]pyrimidin-7-ylamino)-ethoxy]-phenol (Compound 22; 0.13 g) as a yellow powder, which was used without further purification in the next step: ESIMS m/z 303.0 ([M+H]+).

Workup

  1. customequipped with a dry nitrogen line at 25° C
  2. waitAfter 24 h
  3. customa dark yellow solid precipitated
  4. customwas removed by filtration
  5. extractionThe filtrate was extracted with EtOAc (2×50 mL)
  6. filtrationthe pooled organic fractions were filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec6c8febea3c4bf99f238c549cdb5e23
Source dataset
uspto-grants-2014_12
Patent number
US08921382B2

Reaction notes

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