Stannous chloride dihydrate → HCID 52932180, compound

HRID 2042231Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[S:22][CH:21]=[C:20]([C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:29][C:25]1[CH:24]=[C:23]([C:20]2[C:18]3[N:19]=[C:14]([NH:13][C:10]4[CH:11]=[N:12][C:7]([N:4]5[CH2:5][CH2:6][O:1][CH2:2][CH2:3]5)=[CH:8][CH:9]=4)[N:15]=[CH:16][C:17]=3[S:22][CH:21]=2)[CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(6-Morpholinopyridin-3-yl)-7-(3-nitro phenyl)thieno[3,2-d]pyrimidin-2-amine (476 mg, 1.10 mmol) was dissolved in ethanol (3.5 mL) and tin(II) chloride dihydrate (1238 mg, 5.48 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. The filtrate was concentrated and the resultant target compound (338 mg, 76%) was used without purification.

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
concentrationThe filtrate was concentrated
customthe resultant target compound (338 mg, 76%) was used without purification

Sources & evidence

ORD record: ord-a883016221274e8ba2379212ccc4c3d5
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586580B2

Reaction notes

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