2-(Tributylstannyl)pyrimidine → HCID 44451295, compound

HRID 638823Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:25][C@@:23]3([CH3:24])[C@@H:19]([CH2:20][C@@H:21]([CH3:31])[C@@H:22]3[C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[C@H:18]3[C:9]2=[C:10]2[C:15]([CH2:16][CH2:17]3)=[CH:14][C:13](=[O:32])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:38]1[N:43]=[CH:42][CH:41]=[CH:40][N:39]=1)CCC>>[CH:28]1([C:26]([C@H:22]2[C@H:21]([CH3:31])[CH2:20][C@H:19]3[C@H:18]4[C:9]([C@@H:8]([C:5]5[CH:4]=[CH:3][C:2]([C:38]6[N:43]=[CH:42][CH:41]=[CH:40][N:39]=6)=[CH:7][CH:6]=5)[CH2:25][C@:23]23[CH3:24])=[C:10]2[C:15](=[CH:14][C:13](=[O:32])[CH2:12][CH2:11]2)[CH2:16][CH2:17]4)=[O:27])[CH2:29][CH2:30]1

Participants

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidine

HCID 68576237(11beta,16alpha,17beta)-11-(4-Bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one

Product 1

HCID 44451295HCID 44451295, compoundYield 17%

Conditions

Temperature: 110 °C

Procedure

According to the procedure described in example 8, (11β,16α,17β)-11-(4-bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one and 2-tributylstannylpyrimidine were heated for four hours at 110° C. to give the title compound (17% yield). 1H NMR (400 MHz, CDCl3): δ 0.32 (s, 3H), 0.83-2.87 (m, 24H), 4.47 (d, J=7.0 Hz, 1H), 5.80 (s, 1H), 7.18 (t, J=4.7 Hz, 1H), 7.28-7.31 (m, 2H), 8.32-8.35 (m, 2H), 8.79 (d, J=4.7 Hz, 2H).

Sources & evidence

ORD record: ord-6bcf4d57f02b417294449847dadc918a
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691836B2

Reaction notes

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