Ammonium Chloride → HCID 22134704, compound

HRID 1826588Notes

Reaction equation

HRID 1826588 reaction equation
C(O[C:4](=[O:15])[CH:5](P(OCC)(OCC)=O)[F:6])C.C([Li])CCC.[NH2:21][C:22]1[C:27]([CH:28]=O)=[CH:26][N:25]=[C:24]([S:30][CH3:31])[N:23]=1.[Cl-].[NH4+]>O1CCCC1.O>[F:6][C:5]1[C:4](=[O:15])[NH:21][C:22]2[N:23]=[C:24]([S:30][CH3:31])[N:25]=[CH:26][C:27]=2[CH:28]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 178418339Butyllithium

Product 1

HCID 22134704HCID 22134704, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1.74 g (10.33 mmol) of (diethoxy-phosphoryl)-fluoro-acetic acid ethyl ester in 20 mL of tetrahydrofuran is cooled to −78° C. and treated dropwise with 12.9 mL (20.65 mmol) of a 1.6 M solution of n-butyl lithium in hexanes. After stirring for 30 minutes at −78° C. the solution is treated with 1.74 g (10.33 mmol) of 4-amino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde (Example 3), allowed to warm to room temperature, and stirred overnight. The reaction is treated with saturated aqueous ammonium chloride, then water. The solid is collected by filtration and washed with diethyl ether to give 2.01 g (92%) of the product.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. filtrationThe solid is collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f8d6334e0b38473c986f4db3a5b14f57
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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