4-Chlorothieno[3,2-d]pyrimidine → 4-[4-(2-Thienylmethoxy)anilino]thieno[3,2-d]pyrimidine hydrochloride

HRID 564788Notes

Reaction equation

HRID 564788 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>CC(O)C>[ClH:1].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[C:3]3[S:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 221128824-(2-Thienylmethoxy)aniline

Product 1

HCID 221128754-[4-(2-Thienylmethoxy)anilino]thieno[3,2-d]pyrimidine hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorothieno[3,2-d]pyrimidine (0.102 g, 0.60 mmol) and 4-(2-thienylmethoxy)-aniline (prepared according to the published method: WO 96/09294) (0.135 g, 0.66 mmol) were reacted in 2-propanol (5 ml) for 2 hours, according to Procedure A. The product was obtained as a grey-green solid (0.138 g, 61%) with m.p. 181-182° C.; (Found: C, 53.64; H, 3.61; N, 11.04. C17H13N3OS2.HCl.0.25H2O requires: C, 53.68; H, 3.84; N, 11.05%); δH [2H6]-DMSO 11.28 (1H, br s, NH), 8.75 (1H, s, 2-H), 8.45 (1H, d, J 7, 6 H or 7 H) 7.45-7.68 (4H, m, 6H or 7H, 2′-H, 6′-H, 5″-H), 6.95-7.28 (4H, m, 3′-H, 5′-H, 3″-H, 4″-H), 5.32 (2H, s, CH2); m/z 339 (M+).

Sources & evidence

ORD record
ord-c06b9d00d40f40b683adfa172f10dfd7
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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