Stannous chloride dihydrate → 7-(3-aminophenyl)-N2-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-2,4-diamine

HRID 1485493Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[N:15]=[C:16]([NH:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=4)[N:17]=[C:18]([NH2:19])[C:13]=3[S:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[N:15]=[C:16]([NH:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=4)[N:17]=[C:18]([NH2:19])[C:13]=3[S:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7-(3-Nitrophenyl)-N2-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-2,4-diamine (400 mg, 0.88 mmol) was dissolved in ethanol (3.0 mL) and tin(II) chloride dihydrate (996 mg, 4.41 mmol) was added. The reaction mixture was stirred at 80° C. for 2 hours. After removing ethanol by distillation under reduced pressure, ammonia water was slowly added to make pH 5. Sodium carbonate was added to thus prepared yellow precipitate until the pH reached 7. The precipitate was filtered and washed several times with ethyl acetate. Concentration of the filtrate yielded the target compound of Example 11 (320 mg, 85% yield).

Workup

customAfter removing ethanol
distillationby distillation under reduced pressure, ammonia water
additionwas slowly added
additionSodium carbonate was added to thus prepared yellow precipitate until the pH
filtrationThe precipitate was filtered
washwashed several times with ethyl acetate

Sources & evidence

ORD record: ord-e3c7efbe813a423ba90311c9f021cc32
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422307B2

Reaction notes

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