Dimethylformamide → 5-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

HRID 315623Notes

Reaction equation

HRID 315623 reaction equation
[CH3:23][Si:24]([CH3:25])([CH3:26])[C:27]#[CH:28].[CH3:29][CH2:30][N:31]([CH2:32][CH3:33])[CH2:34][CH3:35].[CH3:55][N:56]([CH3:57])[CH:58]=[O:59].[CH3:60][CH2:61][O:62][C:63](=[O:64])[CH3:65].[Cl:1][c:2]1[c:3]([CH3:22])[cH:4][c:5](-[c:8]2[n:9][c:10]3[n:11]([c:12]([C:14]([F:15])([F:16])[F:17])[cH:13]2)[n:18][cH:19][c:20]3[I:21])[cH:6][cH:7]1.[Cu:107][I:108].[Pd:66]([Cl:67])[Cl:68].[c:36]1([P:37]([c:38]2[cH:39][cH:40][cH:41][cH:42][cH:43]2)[c:44]2[cH:45][cH:46][cH:47][cH:48][cH:49]2)[cH:50][cH:51][cH:52][cH:53][cH:54]1.[c:69]1([P:70]([c:71]2[cH:72][cH:73][cH:74][cH:75][cH:76]2)[c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[cH:83][cH:84][cH:85][cH:86][cH:87]1.[c:88]1([P:89]([c:90]2[cH:91][cH:92][cH:93][cH:94][cH:95]2)[c:96]2[cH:97][cH:98][cH:99][cH:100][cH:101]2)[cH:102][cH:103][cH:104][cH:105][cH:106]1>>[Cl:1][c:2]1[c:3]([CH3:22])[cH:4][c:5](-[c:8]2[n:9][c:10]3[n:11]([c:12]([C:14]([F:15])([F:16])[F:17])[cH:13]2)[n:18][cH:19][c:20]3[C:28]#[C:27][Si:24]([CH3:23])([CH3:25])[CH3:26])[cH:6][cH:7]1

Participants

9

Reactant 8

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine3×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 670008925-(4-Chloro-3-methyl-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670004775-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

Sources & evidence

ORD record
ord-960224f164f24d54985f39761f048a3a
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (8/10)

Reaction notes

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