Hydrochloric Acid → 5-(2-aminoethyl)-N-[3-chloro-4-(3-chlorophenoxy)phenyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride

HRID 1926103Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:18]3[N:25]([CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[CH:24]=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1.[ClH:36]>O1CCCC1>[ClH:1].[ClH:36].[NH2:28][CH2:27][CH2:26][N:25]1[C:18]2[C:17]([NH:16][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=4)=[C:2]([Cl:1])[CH:3]=3)=[N:22][CH:21]=[N:20][C:19]=2[CH:23]=[CH:24]1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of tert-butyl 2-(4-{[3-chloro-4-(3-chlorophenoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethylcarbamate (1.69 g) in tetrahydrofuran (32 mL) was added 2N hydrochloric acid (16 mL). The reaction mixture was stirred at 65° C. for 18 hrs and concentrated. Ethanol was added, and the mixture was concentrated again. Ethyl acetate and diisopropyl ether were added to the residue, and the precipitate was collected by filtration and washed with diisopropyl ether to give the title compound (1.50 g) as crystals.

Workup

concentrationconcentrated
additionEthanol was added
concentrationthe mixture was concentrated again
additionEthyl acetate and diisopropyl ether were added to the residue
filtrationthe precipitate was collected by filtration
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-a7dd9d52b36146bab497485973f49ba7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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