3-Bromo-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine → HCID 178508588, compound

HRID 500652Notes

Reaction equation

HRID 500652 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[N:3]=1.BrC1C2C(=NC=NC=2N)N(C(C)(C)C)N=1.[CH:39]1[C:47]2[C:46]3[CH:48]=[CH:49][CH:50]=[CH:51][C:45]=3[S:44][C:43]=2[CH:42]=[C:41](B(O)O)[CH:40]=1>>[CH:39]1[C:47]2[C:46]3[CH:48]=[CH:49][CH:50]=[CH:51][C:45]=3[S:44][C:43]=2[CH:42]=[C:41]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[N:4]([C@H:12]3[CH2:17][CH2:16][C@H:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[N:3]=2)[CH:40]=1

Participants

4

Reactant 3

HCID 585971453-Bromo-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 58988720Dibenzothiophene-3-boronic acidHCID 178508630HCID 178508630, compound

Product 1

HCID 178508588HCID 178508588, compound

Procedure

The desired product was prepared by substituting (trans)-3-iodo-1-(4-morpholin-4-yl-cyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine prepared as described in WO 2005/074603 for 3-bromo-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine and dibenzo(b,d)thiophen-3-ylboronic acid (purchased from Maybridge Chemicals) for EXAMPLE 188C in EXAMPLE 181. 1H NMR (300 MHz, methanol-d4) 8.56 (d, 1H), 8.40 (s, 1H), 8.34 (m, 1H), 8.12 (d, 1H); 7.96 (m, 1H); 7.80 (d, 1H); 7.54 (m, 2H); 4.95 (m, 1H); 4.12 (m, 2H); 3.80 (m, 2H); 3.58-3.38 (m, 4H); 2.44-2.38 (m, 2H); 2.38-2.25 (m, 4H); 1.94-1.82 (m, 2H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-7823429c39eb435a8f54774098e2aea9
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

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