Sodium Bicarbonate → HCID 11625608, compound

HRID 1365897Notes

Reaction equation

HRID 1365897 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:16]=[C:15](Br)[CH:14]=[C:13]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[CH3:24][O:25][C:26]1[N:31]=[CH:30][C:29](B(O)O)=[CH:28][N:27]=1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:16]=[C:15]([C:29]3[CH:28]=[N:27][C:26]([O:25][CH3:24])=[N:31][CH:30]=3)[CH:14]=[C:13]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 27367782-Methoxypyrimidine-5-boronic acid2×HCID 86089656HCID 86089656, compound

Product 1

HCID 11625608HCID 11625608, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(3-acetamidophenyl)-4-bromo-6-morpholinopyrimidine (0.037 g), 2-methoxypyrimidin-5-ylboronic acid (0.019 g), tetrakis(triphenylphosphine)palladium(0) (3 mg), a saturated aqueous sodium bicarbonate solution (0.2 ml) and 1,2-dimethoxyethane (2 ml) was stirred and heated to 60° C. for 18 hours under an atmosphere of nitrogen. A second portion of each of 2-methoxypyrimidin-5-ylboronic acid (0.019 g), tetrakis(triphenylphosphine)palladium(0) (2 mg), a saturated aqueous sodium bicarbonate solution (0.2 ml) and 1,2-dimethoxyethane (1 ml) was added and the resultant mixture was heated to 60° C. for a further 18 hours. The resultant reaction mixture was evaporated and the residue was triturated under a 5:1 mixture (1 ml) of methylene chloride and methanol. The soluble material was purified by column chromatography on reversed-phase silica using an ‘Isolute SCX’ column (1 g; International Sorbent Technology Limited, Mid Glamorgan, UK) by initially washing the column with methanol (5 ml) followed by elution with a 5:3:2 mixture of methanol, methylene chloride and a 7M methanolic ammonia solution. The material so obtained was dried under vacuum. There was thus obtained the title compound as a solid (0.034 g); NMR Spectrum: (DMSOd6) 2.05 (s, 3H), 3.66-3.8 (m, 8H), 3.97 (s, 3H), 7.3-7.37 (m, 2H), 7.82 (d, 1H), 8.03-8.09 (m, 1H), 8.52 (s, 1H), 9.38 (s, 2H), 9.98 (s, 1H); Mass Spectrum: M+H+407.

Workup

  1. customThe resultant reaction mixture
  2. customwas evaporated
  3. customthe residue was triturated under a 5:1 mixture (1 ml) of methylene chloride and methanol
  4. customThe soluble material was purified by column chromatography on reversed-phase silica using an ‘Isolute SCX’ column (1 g; International Sorbent Technology Limited, Mid Glamorgan, UK)
  5. washby initially washing the column with methanol (5 ml)
  6. washfollowed by elution with a 5:3:2 mixture of methanol, methylene chloride
  7. customThe material so obtained
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-c79f999f21f94232b865781c55a28f15
Source dataset
uspto-grants-2011_02
Patent number
US07893063B2

Reaction notes

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