2-Bromopyrimidine → 4-(2-Pyrimidinyl)phenol

HRID 1518366Notes

Reaction equation

HRID 1518366 reaction equation
S1C2C=CC=CC=2N=C1N(COCC[Si](C)(C)C)C(C1C=CC=C2C=1CN(C1SC(C3C=CC(CO)=CC=3)=C(C(OCC)=O)N=1)CC2)=O.OCC1C=CC(B(O)O)=CC=1.Br[C:61]1[N:66]=[CH:65][CH:64]=[CH:63][N:62]=1.CC1(C)C(C)(C)OB([C:75]2[CH:80]=[CH:79][C:78]([OH:81])=[CH:77][CH:76]=2)O1>>[N:62]1[CH:63]=[CH:64][CH:65]=[N:66][C:61]=1[C:75]1[CH:80]=[CH:79][C:78]([OH:81])=[CH:77][CH:76]=1

Participants

5

Reactant 4

HCID 783452-BromopyrimidineHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 59447480ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylate

Product 1

HCID 1358026824-(2-Pyrimidinyl)phenol

Procedure

Compound 81A was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with 2-bromopyrimidine and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.92 (s, 1H), 8.80 (d, J=4.6 Hz, 2H), 8.22-8.26 (m, 2H), 7.31 (t, J=4.6 Hz, 1H), 6.89-6.89 (m, 2H).

Sources & evidence

ORD record
ord-341ee14dc32a47278ee3db1c0e40eb35
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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