Cesium carbonate → HCID 178484427, compound

HRID 1672473Notes

Reaction equation

HRID 1672473 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19]4[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=4)[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:33][CH2:34][N:35]([CH3:43])[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39]>CN(C=O)C>[OH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH2:33][CH2:34][N:35]([CH3:43])[C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:23][CH:24]=4)[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 59840485tert-Butyl N-(2-chloroethyl)-N-methylcarbamateHCID 178515847HCID 178515847, compound

Product 1

HCID 178484427HCID 178484427, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To the flask were added 4-{2-[(trans-4-hydroxycyclohexyl)amino]quinazolin-8-yl}phenol (110 mg, 0.33 mmol), Cs2CO3 (1345 mg, 4.13 mmol), tert-butyl (2-chloroethyl)methylcarbamate (290 mg, 1.45 mmol) and DMF (5 mL). The mixture was stirred for 3 hours at 85° C. The reaction was completed as judged by TLC. The mixture was concentrated in vacuo to afford crude tert-butyl [2-(4-{2-[(trans-4 hydroxycyclohexyl)amino]quinazolin-8-yl}phenoxy)ethyl]methylcarbamate

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-03c66221ae904dea953d0f96aa7e017a
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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