Ethanol → tert-Butyl 6-[2-(cyclopropyl)pyrimidin-5-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2334890Notes

Reaction equation

HRID 2334890 reaction equation
[Br:53][c:54]1[cH:55][n:56][c:57]([CH:60]2[CH2:61][CH2:62]2)[n:58][cH:59]1.[CH3:109][CH2:110][OH:111].[CH3:112][c:113]1[cH:114][cH:115][cH:116][cH:117][cH:118]1.[CH3:1][C:2]1([CH3:3])[C:4]([CH3:5])([CH3:6])[O:7][B:8]([c:9]2[cH:10][c:11]3[c:16]([cH:17][cH:18]2)[CH2:15][N:14]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:13][CH2:12]3)[O:26]1.[CH3:27][C:28]1([CH3:29])[C:30]([CH3:31])([CH3:32])[O:33][B:34]([c:35]2[cH:36][cH:37][cH:38][c:39]3[c:40]2[CH2:41][N:42]([C:43]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:49])[CH2:50][CH2:51]3)[O:52]1.[Fe+2:108].[Na+:63].[Na+:64].[O-:65][C:66](=[O:67])[O-:68].[Pd:69]([Cl:70])[Cl:71].[cH:72]1[cH:73][cH:74][c:75]([P:76]([c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[c-:83]2[cH:84][cH:85][cH:86][cH:87]2)[cH:88][cH:89]1.[cH:90]1[cH:91][cH:92][c:93]([P:94]([c:95]2[cH:96][cH:97][cH:98][cH:99][cH:100]2)[c-:101]2[cH:102][cH:103][cH:104][cH:105]2)[cH:106][cH:107]1>>[c:9]1(-[c:54]2[cH:55][n:56][c:57]([CH:60]3[CH2:61][CH2:62]3)[n:58][cH:59]2)[cH:10][c:11]2[c:16]([cH:17][cH:18]1)[CH2:15][N:14]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:13][CH2:12]2

Participants

11

Reactant 10

HCID 702EthanolHCID 923Sodium ion2×HCID 1140TolueneHCID 19660Carbonate IonHCID 24290Palladium ChlorideHCID 27284Ferrous cationHCID 204444135-Bromo-2-cyclopropylpyrimidineHCID 52987621(2-(Tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-YL)boronic acid pinacol esterHCID 66734880tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 178420532HCID 178420532, compound2×

Product 1

HCID 66734991tert-Butyl 6-[2-(cyclopropyl)pyrimidin-5-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Sources & evidence

ORD record
ord-be7cd852c8744a4488807c88cc2f4c96
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (10/10)

Reaction notes

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