Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate → Allyl trans-2-[3-(7-Bromo-6-chloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate

HRID 4273Notes

Reaction equation

HRID 4273 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[Cl:12].[CH3:13][O:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[C@H:16]1[CH2:27][C:28](=[O:31])[CH2:29]Br>>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]([CH2:29][C:28](=[O:31])[CH2:27][C@H:16]3[C@H:15]([O:14][CH3:13])[CH2:20][CH2:19][CH2:18][N:17]3[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[C:10](=[O:11])[C:5]=2[S:4][C:3]=1[Cl:12]

Participants

3

Reactant 2

HCID 86741991Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylateHCID 1355834887-bromo-6-chlorothieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 70393392Allyl trans-2-[3-(7-Bromo-6-chloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate

Procedure

According to the method of Example 4, 0.662 g (0.0025 mole) of 7-bromo-6-chlorothieno[3,2-d]pyrimidin-4(3H)-one and 1.24 g (0.0037 mole) of allyl trans-3-methoxy-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate were combined to give the title compound: yield 0.90 g (69%); 1H-nmr (CDCl3) delta 1.3-2.1 ppm (multiplet, 4H, OCHCH2CH2CH2N), 2.7-3.1 (multiplet, 4H, COCH2CH and NCH2), 3.3 (broad singlet, 1H, CH2CHNCO), 3.4 (singlet, 3HOCH3), 4.0 (broad doublet, 1H, CHOCH3), 4.6 (broad doublet, 2H, CH2CH=CH2), 4.9-5.1 (multiple peaks, 2H, NCH2CO), 5.3 (triplet with fine splitting, 2H, CH2 =CH), 5.9 (octet, 1H, CH=CH2), 7.2 [singlet, 0.15H, thieno H (some of the 6-chloro analog, an impurity)], 8.0 [broad singlet, 0.15H, (N=CH--N from the 6-chloro analog)], 8.1 (broad singlet, 1H, N=CH--N).

Sources & evidence

ORD record
ord-7e66be7c0e9d4c90b088462789db9336
Source dataset
uspto-grants-1988_02
Patent number
US04725599

Reaction notes

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