Ethyl 4-[4-(4-cyclohexylamino-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]benzoate → tert-butyl {(1S,2S)-2-[2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino]cyclopentyl}carbamate

HRID 2240115Notes

Reaction equation

[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:13][C:14]1[C:15]2[S:23][CH2:22][CH2:21][C:16]=2[N:17]=[C:18](Cl)[N:19]=1)([CH3:4])([CH3:3])[CH3:2].C1(NC2C3SCCC=3N=C([N:38]3[CH2:43][CH2:42][N:41]([C:44]4[CH:54]=[CH:53][C:47](C(OCC)=O)=[CH:46][CH:45]=4)[CH2:40][CH2:39]3)N=2)CCCCC1>O1CCOCC1>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:13][C:14]1[C:15]2[S:23][CH2:22][CH2:21][C:16]=2[N:17]=[C:18]([N:38]2[CH2:43][CH2:42][N:41]([C:44]3[CH:54]=[CH:53][CH:47]=[CH:46][CH:45]=3)[CH2:40][CH2:39]2)[N:19]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

1.08 g (2.9 mmol) of tert-butyl[(1S,2S)-2-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)cyclopentyl]carbamate (V) (chiral) and 9.9 mmol of 1-phenylpiperazine (VI) are placed in 14 mL of dioxane, then heated to 160° C. for 2.3 hours. The reaction mixture is concentrated by evaporation, the residue is then purified by HPLC through an RP column (column: XTerra, MS-C18, 5 μm, 19*100 mm, eluant: water+0.1% trifluoroacetic acid (A), acetonitrile+0.1% trifluoroacetic acid (B)).

Workup

concentrationThe reaction mixture is concentrated by evaporation
customthe residue is then purified by HPLC through an RP column (column: XTerra, MS-C18, 5 μm, 19*100 mm, eluant: water+0.1% trifluoroacetic acid (A), acetonitrile+0.1% trifluoroacetic acid (B))

Sources & evidence

ORD record: ord-3734e1e2299649618719519913edfc08
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723341B2

Reaction notes

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