Potassium Carbonate → 4-(4-Methyl-piperazin-1-yl)-6,7,8,9-tetrahydro-benzo[4,5]thieno[3,2-d]pyrimidin-2-ylamine

To a solution of 4-chloro-6,7,8,9-tetrahydro-benzo[4,5]thieno[3,2-d]pyrimidin-2-ylamine (0.09 mg, 0.37 mmol) in EtOH (3.7 mL) was added K2CO3 (0.12 g, 0.84 mmol) followed by N-methylpiperazine (0.05 mL, 0.44 mmol). After stirring at rt for 22 h, EtOH was removed under reduced pressure and the mixture was dissolved in CH2Cl2 (5 mL) and poured over H2O (10 mL). The aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with brine, such as with a satd. aq. NaCl, (30 mL), dried, for example with Na2SO4, and concentrated to afford the title compound (0.05 g) as a pale yellow solid. MS: 304.2. 1H NMR (400 MHz, CD3OD) δ ppm 3.93-3.88 (m, 4H), 2.80 (t, J=6.0 Hz, 2H), 2.63 (t, J=6.1 Hz, 2H), 2.56-2.52 (m, 4H), 2.33 (s, 3H), 1.96-1.81 (m, 4H).

1. customEtOH was removed under reduced pressure
2. dissolutionthe mixture was dissolved in CH2Cl2 (5 mL)
3. additionpoured over H2O (10 mL)
4. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 mL)
5. washThe combined organic layers were washed with brine, such as with a satd
6. concentrationconcentrated

ORD record

ord-c6a3b02272d649569855a7bfe38783d5

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927555B2