Hydrochloric Acid → 4-[2-(Thiazolo[5,4-d]pyrimidin-7-ylamino)-ethyl]-phenol

HRID 1409286Notes

Reaction equation

Cl[C:2]1[C:3]2[N:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[N:10]1[C:3]2[C:2]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-Chlorothiazolo[5,4-d]pyrimidine (2.71 grams (g), 15.7 millimoles (mmol)) and tyramine (2.16 g, 15.7 mmol) were dissolved with magnetic stirring in N,N-dimethylformamide (DMF; 20 milliliters (mL)) in a 100 mL round bottom flask equipped with a reflux condenser and a dry nitrogen line at 25° C. To the solution was added potassium carbonate (K2CO3; 6.0 g, 43.4 mmol), and the mixture was heated at 100° C., then cooled to 25° C., and stirred overnight. The reaction was diluted with water (H2O; 150 mL), and then treated with 2 N hydrochloric acid (HCl) to adjust the pH to 6. The aqueous layer was washed repeatedly with EtOAc, and the pooled organic fractions were filtered and concentrated in vacuo to provide 4-[2-(thiazolo[5,4-d]pyrimidin-7-ylamino)-ethyl]-phenol (Compound 3; 1.0 g) as an amber powder: mp 161-168° C.; 1H NMR (DMSO-d6) δ 9.24 (s, 1H), 9.18 (s, 1H), 8.42 (s, 1H), 8.29 (br s, 1H), 7.04 (d, J=8.0 Hz, 2H), 6.67 (d, J=8.3 Hz, 2H), 3.65 (m, 2H), 2.81 (m, 2H); ESIMS m/z 273.1 ([M+H]+).

Workup

customequipped with a reflux condenser
customat 25° C
temperaturecooled to 25° C.
washThe aqueous layer was washed repeatedly with EtOAc
filtrationthe pooled organic fractions were filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4395fdd31d1d49949331ccece58fa92f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921382B2

Reaction notes

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