Guanidine → 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine

HRID 280029

반응식

HRID 280029 반응식
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].NC(N)=N.[CH3:13][O:14][C:15]1[CH:24]=[C:23]([CH:25]=[C:26]([CH2:29]OC)[C:27]#[N:28])[C:18]2[CH:19]=[CH:20][CH2:21][O:22][C:17]=2[C:16]=1[O:32][CH3:33]>CO>[NH2:4][C:3]1[N:5]=[C:27]([NH2:28])[C:26]([CH2:25][C:23]2[C:18]3[CH:19]=[CH:20][CH2:21][O:22][C:17]=3[C:16]([O:32][CH3:33])=[C:15]([O:14][CH3:13])[CH:24]=2)=[CH:29][N:2]=1

참가 물질

6

반응물 4

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 543734473-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile

생성물 1

HCID 128497722,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine수율 42.8%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
3 °C

실험 절차

Guanidine hydrochloride (11.46 g, 0.12 mole) in methanol (25 mL) was added to sodium methoxide (6.55 g, 0.12 mole) in methanol (40 mL) and the resultant sodium chloride was filtered and washed with methanol (10 mL). The guanidine solution was added to 3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile (11.5 g, 0.04 mole) and the mixture heated at reflux for 2 hr. Cooling the mixture at 3° C. provided 5.38 g of yellow solid in two crops. HPLC assayed yield of 28.6%. A sample recrystallized from alcohol/water gave mp 232°-4° C.

후처리

  1. filtrationthe resultant sodium chloride was filtered
  2. washwashed with methanol (10 mL)
  3. temperaturethe mixture heated
  4. temperatureat reflux for 2 hr

출처 및 근거

ORD 기록
ord-9e768bf9bff745e0b5c3dd1a637c04c9
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587342

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