Potassium Carbonate → Tert-butyl[3-(2-{5-[(2,5-dichloropyrimidin-4-yl)amino]-2-methoxyphenyl}ethyl)phenyl]carbamate

HRID 541574Notes

Reaction equation

HRID 541574 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]1[N:38]=[C:37](Cl)[C:36]([Cl:40])=[CH:35][N:34]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([NH:22][C:35]3[C:36]([Cl:40])=[CH:37][N:38]=[C:33]([Cl:32])[N:34]=3)[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 89143988Tert-butyl{3-[2-(5-amino-2-methoxyphenyl)ethyl]phenyl}carbamate

Product 1

HCID 57962445Tert-butyl[3-(2-{5-[(2,5-dichloropyrimidin-4-yl)amino]-2-methoxyphenyl}ethyl)phenyl]carbamateYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl{3-[2-(5-amino-2-methoxyphenyl)ethyl]phenyl}carbamate (55 mg, 0.16 mmol), potassium carbonate (67 mg, 0.48 mmol), and 2,4,5-trichloropyrimidine (18 μL, 0.16 mmol) were stirred in N,N-dimethylformamide (1.5 mL) for 30 minutes. Purification by preparative LCMS (pH 2) gave the desired compound (75 mg, 95%). 1H NMR (300 MHz, DMSO-d6): δ 9.40 (s, 1H), 9.25 (s, 1H), 8.30 (s, 1H), 7.40 (m, 3H), 7.20 (m, 1H), 7.12 (m, 1H), 6.99 (d, 1H) 6.80 (d, 1H), 3.80 (s, 3H), 2.77 (m, 4H), 1.42 (s, 9H). LCMS for C24H27Cl2N4O3 (M+H)+: m/z=489.1.

Workup

  1. customPurification by preparative LCMS (pH 2)

Sources & evidence

ORD record
ord-f0f9840a12694fe481a0a029a4399402
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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