Triethylamine → HCID 178476961, compound

HRID 1525221Notes

Reaction equation

HRID 1525221 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.Cl.[NH2:18][CH:19]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[C:20]1[CH:21]=[C:22]([P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])[CH:23]=[CH:24][CH:25]=1.CCN(CC)CC>O=S(Cl)Cl.C(Cl)Cl>[OH:1][C:2]1[C:7]([C:8]([NH:18][CH:19]([C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)[C:20]2[CH:21]=[C:22]([P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])[CH:23]=[CH:24][CH:25]=2)=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89462529Diethyl 3-(amino(4-methoxyphenyl)methyl)phenylphosphonate hydrochlorideHCID 178524750HCID 178524750, compound

Product 1

HCID 178476961HCID 178476961, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

The 4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid, 1-1-h, (500 mg, 2.3 mmol) was dissolved in SOCl2 (10 ml), the mixture was stirred at RT for 3 hours, then concentrated under vacuo. The residue was dissolved with 20 ml DCM, and dropwise to a solution of diethyl 3-(amino(4-methoxyphenyl)methyl)phenylphosphonate hydrochloride (5-d, 802 mg, 2.30 mmol) and Et3N (464 mg, 4.6 mmol) in DCM (30 ml) at 0° C., the mixture was stirred at room temperature overnight. Then added water, the water phase was concentrated under vacuo and purified on silica gel chromatography to provide the product, 5-e, (990 mg, 78.4%).

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe residue was dissolved with 20 ml DCM
  3. concentrationThen added water, the water phase was concentrated under vacuo
  4. custompurified on silica gel chromatography

Sources & evidence

ORD record
ord-1eaa0816fd8f4b68a64a1cc78ef9f572
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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