Water → 2-Amino-6-(2-furyl)pyrimidine-4-carbonitrile

HRID 254152ノート

反応式

HRID 254152 の反応式
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.[Na].[N:15]12CCN(CC1)C[CH2:16]2.O>CS(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([C:16]#[N:15])[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 9237Dabco2 回HCID 5360545SodiumHCID 223243064-Chloro-6-(2-furanyl)-2-pyrimidinamine

生成物 1

HCID 668464412-Amino-6-(2-furyl)pyrimidine-4-carbonitrile収率 762.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

A solution of 2-amino-4-chloro-6-(2-furyl)pyrimidine (9.78 g, 50.0 mmol) in DMSO (200 mL) was treated with sodium cyamide (14.7 g, 300 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.56 g, 5.0 mmol). The suspension was stirred for 4 days, and more DABCO (5.04 g, 45 mmol) and DMSO (100 mL) were added. The suspension was stirred for a further 2 days, poured onto a mixture of ice (750 g) and water (750 mL), the crude product was filtered off, washed with water and MeCN, and dried in air to give the title compound (7.1 g, 77%) as a brown solid; m.p. 193-194° C.; NMR δH (400 MHz, DMSO) 6.74 (1H, q, J 1.6 Hz), 7.32 (2H, br s), 7.39 (1H, d, J 3.6 Hz), 7.43 (1H, s) and 7.98 (1H, d, J 1.2 Hz); M/Z 187 (M+H)+.

後処理

  1. stirringThe suspension was stirred for a further 2 days
  2. filtrationthe crude product was filtered off
  3. washwashed with water and MeCN
  4. customdried in air

出典と根拠

ORDレコード
ord-1f3484034b8a470c9a3bcc701089f92f
出典データセット
uspto-grants-2011_01
特許番号
US07875600B2

反応ノート

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