1,2-Dichloroethane → N-(Cyclopropylmethyl)-3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzamide

HRID 2243648Notes

Reaction equation

HRID 2243648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22](O)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31].C(Cl)CCl.C1[CH:37]=[CH:38][C:39]2N(O)N=[N:42][C:40]=2C=1.C1(CN)CC1>C(Cl)Cl>[CH:39]1([CH2:40][NH:42][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:27]([CH3:28])=[C:19]([C:18]3[C:13]4[CH2:12][NH:11][C:10](=[O:31])[N:9]([C:3]5[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=5[F:8])[C:14]=4[N:15]=[C:16]([S:29][CH3:30])[N:17]=3)[CH:20]=2)[CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 119506223-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid

Product 1

HCID 11949927N-(Cyclopropylmethyl)-3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid (500 mg) in methylenechloride (100 mL) were added EDC (260 mg), HOBt (160 mg) and cyclopropylmethylamine (260 uL). The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified via column chromatography to provide the title compound as a white solid. LC-MS m/z 496 (M+H)+, 2.62 min (ret. time).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified via column chromatography

Sources & evidence

ORD record
ord-802b25aa7afc4e3e87e1b6b1a7721a94
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

Loading…