Water → HCID 178418729、化合物

HRID 473994

反応式

HRID 473994 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.C(NC(C)C)(C)C.[NH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1.O>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:18][C:19]2[NH:20][N:21]=[C:22]([CH3:24])[CH:23]=2)[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 7912DiisopropylamineHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 931461H-Pyrazol-3-amine, 5-methyl-

生成物 1

HCID 178418729HCID 178418729、化合物収率 67.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 4,6-dichloro-2-(methylthio)pyrimidine (25 g, 0.128 mol) in DMF (100 ml) was added diisopropylamine (19.8 g, 0.154 mol) followed by 3-amino-5-methylpyrazole (13.7 g, 0.154 mol) portionwise over 10 minutes. The solution was heated to 50° C. for 16 hours, after which time all of the starting material had reacted (by LC/MS analysis). The mixture was cooled to ambient and poured into water (250 ml). The precipitate was filtered and the wet solid slurried in diethyl ether (300 ml). The solid was again filtered and re-slurried in methanol (100 ml). The filtered product was air dried on the sinter, then further dried under vacuum. This affords the title compound as an off-white solid (22.1 g, 66% yield). 1H NMR (d6-DMSO) δ 2.22 (3H, s, CH3), 3.31 (3H, s, CH3), 6.00-7.50 (2H, br, CH), 10.17 (1H, s, NH), 12.10 (1H, s, NH); MS ES+256.08, ES−254.25.

後処理

  1. customafter which time all of the starting material had reacted (by LC/MS analysis)
  2. temperatureThe mixture was cooled to ambient and
  3. filtrationThe precipitate was filtered
  4. filtrationThe solid was again filtered and re-slurried in methanol (100 ml)
  5. customdried on the sinter
  6. customfurther dried under vacuum

出典と根拠

ORDレコード
ord-d250ddb18857464dbbd7e042437ef21b
出典データセット
uspto-grants-2014_01
特許番号
US08637511B2

関連ノート

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