Sodium Carbonate → HCID 68648285, compound

HRID 1162571Notes

Reaction equation

HRID 1162571 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][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[N:7]=[C:6]([NH:8][CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:5]=[CH:4][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 623440534-Pyrimidinamine, 2-chloro-N-cyclopentyl-

Product 1

HCID 68648285HCID 68648285, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 178420554HCID 178420554, compoundCatalyst

Procedure

(2-chloro-pyrimidin-4-yl)-cyclopentylamine (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 Q2, to give 164 mg of [2-(4-benzyloxy-phenyl)-pyrimidin-4-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-c139bf4d59ae425190c135915d36cfff
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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