Triethylamine → (1-Pyrimidin-4-yl-cyclopropyl)-carbamic acid tert-butyl ester

HRID 1040484Notes

Reaction equation

HRID 1040484 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11](=O)/[CH:12]=[CH:13]/[N:14](C)[CH3:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([N:21](CC)CC)C.Cl.C(N)=N>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][N:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 67291958(E)-tert-butyl 1-(3-(dimethylamino)acryloyl)cyclopropylcarbamate

Product 1

HCID 67292536(1-Pyrimidin-4-yl-cyclopropyl)-carbamic acid tert-butyl esterYield 20.4%

Conditions

Temperature
77.5 °C

Procedure

To a solution of [1-((E)-3-Dimethylamino-acryloyl)-cyclopropyl]-carbamic acid tert-butyl ester (600 mg, 2.4 mmol) was added triethylamine (1.3 mL, 9.4 mmol) and formamidine hydrochloride (570 mg, 7.1 mmol) at room temperature. The reaction was stirred at 75-80° C. for 14 h. The volatiles were removed in vacuo to give a crude solid mass that was purified by preparative reversed phase HPLC to give 115 mg of the title compound as a light yellow solid, m/z 236.36 [M+1]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customto give a crude solid mass that
  3. customwas purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-2544949b8aa049d39cd830e4ab4a5829
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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