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

HRID 254152노트

반응식

HRID 254152 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 9237Dabco2회HCID 5360545SodiumHCID 223243064-Chloro-6-(2-furanyl)-2-pyrimidinamine

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-1f3484034b8a470c9a3bcc701089f92f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875600B2

반응 노트

불러오는 중…