Hydrochloric Acid → 3-Chloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride

HRID 38552

Reaction equation

[Cl:1][C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:22][C:23]1[CH:24]=[C:25]([OH:30])[CH:26]=[C:27]([Cl:29])[CH:28]=1.Cl.O1CCOCC1>CC(O)C.O1CCOCC1>[ClH:1].[Cl:29][C:27]1[CH:26]=[C:25]([OH:30])[CH:24]=[C:23]([NH:22][C:2]2[C:3]3[C:10]4[CH2:11][CH2:12][NH:13][CH2:14][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-chloro-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate from Example 11A (3.24 g, 9.95 mmol) was dissolved in 2-propanol (40 mL). 3-Amino-5-chlorophenol (1.50 g, 10.4 mmol) from Example 64A and a 4 M solution of gaseous hydrogen chloride in dioxane (124 μL, 0.50 mmol) were added, and the mixture was heated to 80° C. for 20 h. Subsequently, further hydrogen chloride in dioxane (5.0 mL, 20 mmol) was added, and the mixture was heated for additional 3 h. The resulting precipitate was collected by suction filtration to yield 3.63 g (99%) of the title compound.

Workup

temperaturethe mixture was heated for additional 3 h
filtrationThe resulting precipitate was collected by suction filtration

Sources & evidence

ORD record: ord-c6ce6b161be24a09b29701d770620561
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Linked notes

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