Sodium hydride → 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432151

반응식

HRID 432151 반응식
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[NH:16][N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH:37]2[CH2:46][CH2:45][C:40]3([O:44][CH2:43][CH2:42][O:41]3)[CH2:39][CH2:38]2)(=O)=O)=CC=1>CC(N(C)C)=O>[O:41]1[C:40]2([CH2:45][CH2:46][CH:37]([N:16]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:23])=[C:22]4[C:14]([C:11]4[CH:12]=[CH:13][C:8]([O:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[CH:9][CH:10]=4)=[N:15]3)[CH2:38][CH2:39]2)[O:44][CH2:43][CH2:42]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)2회HCID 178508717HCID 178508717, 화합물2회

생성물 1

HCID 223467671-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
105 °C

실험 절차

4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine (Compound 15) (4.9 g) in 200 mL dry dimethylacetamide was treated under nitrogen with 60% sodium hydride (2.0 g) and stirred 30 minutes. 1,4-dioxaspiro[4.5]dec-8-yl 4-methyl-1-benzenesulfonate (Intermediate Y) (15 g) was added and the mixture heated at 105° C. for 42 hours. Evaporation in vacuo and treating with water gave solid which was collected and washed well with water then dried in air. The solid was boiled with diethyl ether (6×120 mL) and the filtered solution evaporated. Treatment with acetone gave 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine as an off-white solid which was collected and washed with acetone then dried in air m.p. 200-202.5° C. Calculated for C25H25N5O3 C 67.7 H 5.6 N 15.8 Found C 67.6H5.8 N15.4.

후처리

  1. customEvaporation in vacuo
  2. additiontreating with water
  3. customgave solid which
  4. customwas collected
  5. washwashed well with water
  6. customthen dried in air
  7. customthe filtered solution evaporated

출처 및 근거

ORD 기록
ord-06b4f547c236407ebcd42bb8805c19d0
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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