Guanidine Hydrochloride → 5-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine

HRID 38430

反応式

HRID 38430 の反応式
[CH2:1]([C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:6]([CH3:12])=[CH:5][C:4]=1[O:13][C:14](=[CH:17]NC1C=CC=CC=1)[C:15]#[N:16])[CH3:2].Cl.[NH2:26][C:27]([NH2:29])=[NH:28].C[O-].[Na+]>C(O)C.O>[CH2:1]([C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:6]([CH3:12])=[CH:5][C:4]=1[O:13][C:14]1[C:15]([NH2:16])=[N:28][C:27]([NH2:29])=[N:26][CH:17]=1)[CH3:2]

参加物

6

反応物 3

HCID 5742Guanidine Hydrochloride2 回HCID 10942334Sodium Methoxide2 回HCID 670534132-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile

生成物 1

HCID 161192635-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine収率 80.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒3 回HCID 962Water溶媒

実験手順

2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile (360 mg, 1 mmol), guanidine HCl (411 mg, 4 mmol) and sodium methoxide (880 ul, 4 mmol, 4.9 M solution in methanol) in 5 mL absolute ethanol were heated to reflux in 5 ml absolute ethanol for 2 hours. Premixed guanidine HCl (411 mg, 4 mmol) and sodium methoxide (880 ul, 4 mmol, 4.9 M solution in methanol) in 1 ml EtOH was added via pipette, and the reaction mixture was heated to reflux for 2 hours. The reaction mixture was cooled, diluted with water, extracted twice with EtOAc, washed with brine, and dried over magnesium sulfate. Solvent was removed in vacuo to give 241 mg of 5-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine as a white solid (74%). Mass Spec M+H=301, M.P.=181° C. Recrystallization of 175 mg of this product from MeOH and HO/diethyl ether afforded 98 mg of the corresponding HCl salt 49%, Mass Spec M+H=301, M.P.>300 C.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted twice with EtOAc
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customSolvent was removed in vacuo

出典と根拠

ORDレコード
ord-80442df476e1479ba91cc59fc93cfaa4
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

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