Tolylboric acid → 6-[3,5-Bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-10-methyl-4-(2-methylphenyl)-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine

HRID 1829648Notes

Reaction equation

[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[C:10]2[N:16]=[C:17]([S:21][CH3:22])[N:18]=[C:19](Cl)[C:9]=2[C:8]1=[O:23].[CH3:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1OB(O)O>>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[C:10]2[N:16]=[C:17]([S:21][CH3:22])[N:18]=[C:19]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[CH3:33])[C:9]=2[C:8]1=[O:23]

Participants

Reactant 2

HCID 13862916Tolylboric acid

HCID 220536006-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine

Product 1

HCID 220535956-[3,5-Bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-10-methyl-4-(2-methylphenyl)-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocineYield 100%

Procedure

In a similar manner to Reference Example 10, 6-[3,5-bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine(Compound of Reference Example 9; 1.25 g) was reacted with 2-methylphenylboric acid (410 mg) to obtain 6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-10-methyl-4-(2-methylphenyl)-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine (1.39 g, 100%).

Sources & evidence

ORD record: ord-c38c0aa9c31647beb0088cf8238d3865
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064119B2

Reaction notes

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