N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine hydrochloride → 4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5,8-dihydro[1]benzothieno[2,3-d]pyrimidin-7(6H)-one hydrochloride

HRID 222030Notes

Reaction equation

HRID 222030 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][CH2:28][C:29]5([CH2:34][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)OCC[O:30]5)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>C(O)(=O)C.O>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][CH2:28][C:29](=[O:30])[CH2:34][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

3

Reactant 1

HCID 67313375N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine hydrochloride

Product 1

HCID 673130304-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5,8-dihydro[1]benzothieno[2,3-d]pyrimidin-7(6H)-one hydrochlorideYield 177.3%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a stirring acetic acid/H2O solution (4:1, 250 mL) was added N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2′-[1,3]dioxolan]-4-amine hydrochloride (10.0 g, 19.3 mmol), and the contents heated at 80° C. for 40 h. The dark colored mixture was cooled to rt, and the solvent removed under reduced pressure. The crude residue was suspended in water (200 mL), stirred for 10 min., and filtered. The collected solid was further washed with H2O (300 mL) and ether (100 mL) to afford the desired product as a brown solid (8.1 g, 89%). 1H-NMR (DMSO-d6) δ 8.71 (d, 1H), 8.54 (s, 1H), 8.42 (s, 1H), 8.10 (td, 1H), 7.78 (d, 1H), 7.75 (d, 1H), 7.56 (m, 2H), 7.25 (d, 1H), 5.38 (s, 2H), 5.08 (br, 1H), 3.76 (s, 2H), 3.50 (t, 2H), 2.69 (t, 2H); LCMS RT=2.44 min; [M+H]+=437.3.

Workup

  1. temperatureThe dark colored mixture was cooled to rt
  2. customthe solvent removed under reduced pressure
  3. filtrationfiltered
  4. washThe collected solid was further washed with H2O (300 mL) and ether (100 mL)

Sources & evidence

ORD record
ord-4da3c71f13ec4457a2c91b413e45043d
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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