Benzonitrile → 5-[3-(3,4-Dihydro-1H-isoquinolin-2-yl)-prop-1-ynyl]-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile
Reaction equation
[Br:14][c:15]1[c:16]([NH:23][CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])[n:17][c:18]([C:21]#[N:22])[n:19][cH:20]1.[C:29]([P:30]([C:31]([CH3:32])([CH3:33])[CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38])([CH3:39])([CH3:40])[CH3:41].[C:58](#[N:59])[c:60]1[cH:61][cH:62][cH:63][cH:64][cH:65]1.[C:66](#[N:67])[c:68]1[cH:69][cH:70][cH:71][cH:72][cH:73]1.[CH2:1]([C:2]#[CH:3])[N:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][CH2:13]1.[CH:42]([NH:43][CH:44]([CH3:45])[CH3:46])([CH3:47])[CH3:48].[Cu:74][I:75].[O:49]1[CH2:50][CH2:51][O:52][CH2:53][CH2:54]1.[Pd:55]([Cl:56])[Cl:57]>>[CH2:1]([C:2]#[C:3][c:15]1[c:16]([NH:23][CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])[n:17][c:18]([C:21]#[N:22])[n:19][cH:20]1)[N:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH2:12][CH2:13]1Participants
9
Reactant 8
HCID 7505Benzonitrile2×
HCID 7912Diisopropylamine
HCID 24290Palladium Chloride
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
HCID 312751,4-Dioxane
HCID 83681Tris(1,1-dimethylethyl)phosphine
HCID 143412942-(Prop-2-yn-1-yl)-1,2,3,4-tetrahydroisoquinoline
HCID 179681615-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrileProduct 1
Sources & evidence
- ORD record
- ord-c784584326804ab783dec990d5d3aa27
- Source dataset
- Test data from https://doi.org/10.1039/C8SC04228D
Reaction notes
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