1,2-Dichloroethane → HCID 57632944, compound

HRID 2109804Notes

Reaction equation

HRID 2109804 reaction equation
COC1C=CC(C2C=NC(N)=NC=2)=CC=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17].C(Cl)CCl.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[N:35][C:36]([NH:39][C:40]3[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][C:48]([OH:50])=O)=[CH:42][CH:41]=3)=[N:37][CH:38]=2)=[CH:29][CH:28]=1.[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.ClCCl.CN1C(=O)CCC1>[CH2:16]([N:18]([CH2:19][CH3:20])[C:48](=[O:50])[CH2:47][CH2:46][C:43]1[CH:42]=[CH:41][C:40]([NH:39][C:36]2[N:37]=[CH:38][C:33]([C:30]3[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[CH:34][N:35]=2)=[CH:45][CH:44]=1)[CH3:17]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 25517Ammonium ChlorideHCID 445585905-(4-Methoxyphenyl)pyrimidin-2-amineHCID 576326193-{4-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionic acid

Product 1

HCID 57632944HCID 57632944, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-(3-Diethylamino-propyl)-phenyl]-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine can be prepared by the following procedure. Diethylamine (10 mmol), EDC (25 mmol) and DMAP (0.1 mmol) are dissolved in dichloromethane (3 mL) and added to the crude 3-{4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionic acid dissolved in NMP (from example 5ao) at rt. After 3 h, sat. aq NH4Cl is added and the mixture is extracted with EtOAc. The combined extracts are dryed over anhydrous Na2SO4 and solvent is removed. Purification by preparative HPLC yields N,N-diethyl-3-{4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionamide.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. customis removed
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-61216388e3c54a0f8d9138045a0ab595
Source dataset
uspto-grants-2009_04
Patent number
US07514447B2

Reaction notes

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