Sodium Bicarbonate → HCID 58504483, compound

HRID 2367270Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[CH:3]=1.[F:19][C:20]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C([O-])(O)=O.[Na+]>O1CCOCC1.O.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>[NH2:8][C:6]1[N:7]=[C:2]([C:26]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([F:19])[CH:27]=2)[CH:3]=[C:4]([NH:9][CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[N:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-chloro-N4-(2,3-dihydro-1H-inden-1-yl)-2,4-pyrimidinediamine (700 mg, 2.69 mmol) and 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (797 mg, 3.23 mmol) in 1,4-dioxane (150 mL) and a solution of NaHCO3 (903 mg, 10.76 mmol) in water (50 mL) was protected with nitrogen. Pd(Ph3P)4 (31 mg, 0.0269 mmol) was added, and the reaction mixture was heated at 120° C. for 16 hours. The mixture was decanted to remove the solids, and the solution was concentrated to dryness. The crude material was purified by SiO2 chromatography eluting with 1:1 THF:petroleum ether to afford the title compound (500 mg) as a yellow solid. LC-MS (ES) m/z=246 [M+H]+.

Workup

customThe mixture was decanted
customto remove the solids
concentrationthe solution was concentrated to dryness
customThe crude material was purified by SiO2 chromatography
washeluting with 1:1 THF

Sources & evidence

ORD record: ord-7c5d263076d44c86a11968468b894827
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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