Allylamine → N-allyl-4-[(3-bromophenyl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

To a 15 mL round-bottom flask were added 50 mg (0.124 mmol, 1 equiv) of 4-[(3-bromophenyl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylic acid, 1, 20 mg (0.124 mmol, 1 equiv) of CDl and THF (1.25 mL). The reaction was stirred for 4 h at rt and then 0.01 mL (0.186 mmol, 1.5 equiv) of allyl amine was added via syringe and the reaction was allowed to stir at rt overnight. The reaction was stopped and THF was concentrated in vacuo and the crude solid was re-dissolved in CH2Cl2 (5 mL). This solution was poured into a separatory funnel and washed with satd NaHCO3 (1×5 mL), water (1×5 mL), and brine (1×5 mL). The organic layer was dried (MgSO4), filtered and concentrated to yield a white solid. The compound was triturated with diethyl ether to yield pure material, 56, as a white solid (36 mg, 66%). 1H-NMR (DMSO-d6) δ 8.42 (s, 1H), 8.31 (s, 1H), 8.19 (t, 1H), 7.86 (m, 1H), 7.63 (m, 1H), 7.25 (m, 2H), 5.82 (m, 1H), 5.08 (m, 2H), 3.75 (t, 2H), 3.21 (m, 2H), 2.97 (d, 2H), 2.69 (m, 1H), 2.15 (m, 1H), 1.82 (m, 1H); LCMS RT=2.78 min; [M+H]+=444.

1. stirringto stir at rt overnight
2. concentrationTHF was concentrated in vacuo
3. dissolutionthe crude solid was re-dissolved in CH2Cl2 (5 mL)
4. additionThis solution was poured into a separatory funnel
5. washwashed with satd NaHCO3 (1×5 mL), water (1×5 mL), and brine (1×5 mL)
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a white solid
10. customThe compound was triturated with diethyl ether
11. customto yield pure material, 56

ORD record

ord-00cdb4fa3bd949208f637ddca55e2c91

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238701B2