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 1788018Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:11][C@H:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.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:44]1([N:41]2[CH2:42][CH2:43][N:38]([C:2]3[N:3]=[C:4]([NH:11][C@H:12]4[CH2:16][CH2:15][CH2:14][C@@H:13]4[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=3)[CH2:39][CH2:40]2)[CH:54]=[CH:53][CH:47]=[CH:46][CH:45]=1

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-cddcdccb875e4adbbf737287a0e71387
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511045B2

Reaction notes

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