Sodium Carbonate → HCID 68648176, compound

HRID 1162569Notes

Reaction equation

HRID 1162569 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(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)C=CC=CC=1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[N:3]=2)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 86079789HCID 86079789, compound

Product 1

HCID 68648176HCID 68648176, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 178420554HCID 178420554, compoundCatalyst

Procedure

(4-chloro-pyrimidin-2-yl)-cyclopentyl-amine (100 mg, 0.51 mmol) was reacted with (4-benzyloxyphenyl)boronic acid (173 mg, 0.76 mmol), tetrakis(triphenylphosphino)palladium (44 mg, 0.04 mmol), and aq. 2 N sodium carbonate (1.01 mmol, 0.51 mL) as described in general procedure Q, method Q1, to give 108 mg (62%) of [4-(4-benzyloxy-phenyl)-pyrimidin-2-yl]cyclopentyl-amine. Purification was carried out by silica gel chromatography eluting with hexanes/ethyl acetate, 4:1 then 1:1. LCMS m/z: 346 (M+1)+.

Sources & evidence

ORD record
ord-17e89a2553b44928a02ce1c3fb761374
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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