N-(3-chloro-4-fluorophenyl)-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine → 4-(3Chloro-4-fluoro-phenylamino)-5,8-dihydro-6H-benzo[4,5]thieno[2,3-d]pyrimidin-7-one

HRID 1787511Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][C:21]5([CH2:26][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)OCC[O:22]5)[CH:5]=[CH:6][C:7]=1[F:8]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][C:21](=[O:22])[CH2:26][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring acetic acid/water solution (4:1, 300 mL) was added N-(3-chloro-4-fluorophenyl)-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2′-[1,3]dioxolan]-4-amine (5.5 g, 14 mmol), and the contents heated at 80° C. for 12 h. The dark colored mixture was cooled to rt, and the solvent was removed under reduced pressure. The crude residue was suspended in aq NaHCO3 (1N, 100 mL), stirred for 10 min, and filtered. The filtered solid was triturated with diethyl ether (100 mL) to afford the desired product (4.8 g, 98%) as a dark yellow solid. 1H-NMR (DMSO-d6) δ 8.53 (s, 1H), 8.46 (s, 1H), 7.87 (dd, 1H), 7.60 (m, 1H), 7.40 (t, 1H), 3.73 (s, 2H), 3.43 (t, 2H), 2.64 (s, 2H); LCMS RT=3.01 min; [M+H]+=348.2.

Workup

temperatureThe dark colored mixture was cooled to rt
customthe solvent was removed under reduced pressure
filtrationfiltered
customThe filtered solid was triturated with diethyl ether (100 mL)

Sources & evidence

ORD record: ord-8990012593484cb688476814d3564ec5
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511048B2

Reaction notes

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