4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 4-(4-(Isopropylamino)thieno[3,2-d]pyrimidin-7-yl)phenol

HRID 1518350Notes

Reaction equation

HRID 1518350 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[C:65]2[N:66]=[CH:67][N:68]=[C:69]([NH:70][CH:71]([CH3:73])[CH3:72])[C:64]=2[S:63][CH:62]=1.CC1(C)C(C)(C)OB([C:82]2[CH:87]=[CH:86][C:85]([OH:88])=[CH:84][CH:83]=2)O1>>[CH:71]([NH:70][C:69]1[C:64]2[S:63][CH:62]=[C:61]([C:82]3[CH:87]=[CH:86][C:85]([OH:88])=[CH:84][CH:83]=3)[C:65]=2[N:66]=[CH:67][N:68]=1)([CH3:73])[CH3:72]

Participants

5

Reactant 4

HCID 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-carboxylateHCID 594476427-bromo-N-isopropylthieno[3,2-d]pyrimidin-4-amine

Product 1

HCID 594475034-(4-(Isopropylamino)thieno[3,2-d]pyrimidin-7-yl)phenol

Procedure

The title compound 69B was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with compound 69A and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.49 (s, 1H), 8.50 (s, 1H), 8.10 (s, 1H), 7.88-7.91 (m, 2H), 7.57 (d, J=7.67 Hz, 1H), 6.83-6.86 (m, 2H), 4.44-4.53 (m, 1H), 1.25 (d, J=6.75 Hz, 6H). ESI (+)/MS: 286 (M−H)+.

Sources & evidence

ORD record
ord-42a9cff2b02540e7b737e9d003ddf2b9
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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