4,4,5,5-tetramethyl-2-(2-methyl-1-benzofuran-3-yl)-1,3,2-dioxaborolane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure A, 4,4,5,5-tetramethyl-2-(2-methylbenzofuran-3-yl)-1,3,2-dioxaborolane and 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 were reacted to give 103. LCMS (MH+)=502.3. 1H-NMR (DMSO-d6): δ 8.55 (m, 1H), 8.19 (d, 1H), 7.86 (d, 1H), 7.56 (m, 1H), 7.32 (m, 2H), 4.48 (s, 4H), 4.01 (s, 1H), 3.85 (m, 4H), 3.72 (s, 2H), 2.96 (s, 3H), 2.93 (m, 2H), 2.01 (m, 2H), 1.66 (m, 2H), 1.29 (m, 2H), 1.25 (m, 1H), 1.04 (s, 6H) were reacted

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure A, 4,4,5,5-tetramethyl-2-(2-methylbenzofuran-3-yl)-1,3,2-dioxaborolane and 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 were reacted to give 103. LCMS (MH+)=502.3. 1H-NMR (DMSO-d6): δ 8.55 (m, 1H), 8.19 (d, 1H), 7.86 (d, 1H), 7.56 (m, 1H), 7.32 (m, 2H), 4.48 (s, 4H), 4.01 (s, 1H), 3.85 (m, 4H), 3.72 (s, 2H), 2.96 (s, 3H), 2.93 (m, 2H), 2.01 (m, 2H), 1.66 (m, 2H), 1.29 (m, 2H), 1.25 (m, 1H), 1.04 (s, 6H) were reacted

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure A, 4,4,5,5-tetramethyl-2-(2-methylbenzofuran-3-yl)-1,3,2-dioxaborolane and 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 were reacted to give 103. LCMS (MH+)=502.3. 1H-NMR (DMSO-d6): δ 8.55 (m, 1H), 8.19 (d, 1H), 7.86 (d, 1H), 7.56 (m, 1H), 7.32 (m, 2H), 4.48 (s, 4H), 4.01 (s, 1H), 3.85 (m, 4H), 3.72 (s, 2H), 2.96 (s, 3H), 2.93 (m, 2H), 2.01 (m, 2H), 1.66 (m, 2H), 1.29 (m, 2H), 1.25 (m, 1H), 1.04 (s, 6H) were reacted

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-amino-2-[4-(5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-ylmethyl)piperazin-1-yl]-2-methylpropan-1-ol (100 mg, 0.23 mmol), 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzofuran (88 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium (26 mg, 0.02 mmol) and Cs2CO3 (148 mg, 0.45 mmol) in dioxane (6 mL) and H2O (3 mL) was purged with argon then heated at 140° C. for 30 min in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with DCM/MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 50-100%) to afford 211 as a cream solid (75 mg, 61%). LCMS (Method G): RT 10.35 min, [M+H]+ 536.4. 1H NMR (CDCl3, 400 MHz): δ 8.40-8.37 (m, 1 H); 7.46-7.42 (m, 1 H); 7.32-7.23 (m, 2 H); 7.10 (d, J=5.3 Hz, 1 H); 5.22 (d, J=5.3 Hz, 1 H); 4.40 (m, 4 H); 3.93-3.87 (m, 6 H); 2.92 (s, 3 H); 2.69 (m, 4 H); 2.62 (m, 4 H) and 1.26 (s, 6 H) was purged with argon was washed with DCM/MeOH the product eluted with 2M NH3/MeOH The resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 50-100%)