Guanidine Hydrochloride → 6-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol

HRID 48457

반응식

HRID 48457 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([O:20]COCC[Si](C)(C)C)[CH:7]=[C:8]([CH2:11][C:12]3[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=3)[CH:9]=2)[CH:4]=[CH:3]1.CC([O-:33])(C)C.[K+].CN1C2C(=C(OCOCC[Si](C)(C)C)C=C(C=O)C=2)C=C1.N(CCC#N)C1C=CC=CC=1.Cl.NC(N)=N>C(O)(C)(C)C.CS(C)=O.C(OCC)(=O)C.C(O)C>[CH3:6][OH:20].[NH4+:2].[OH-:33].[NH2:18][C:15]1[N:14]=[C:13]([NH2:19])[C:12]([CH2:11][C:8]2[CH:7]=[C:6]([OH:20])[C:5]3[CH:4]=[CH:3][N:2]([CH3:1])[C:10]=3[CH:9]=2)=[CH:17][N:16]=1

참가 물질

11

반응물 5

HCID 5742Guanidine HydrochlorideHCID 141003-AnilinopropionitrileHCID 227428761-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indole-6-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 699224535-[1-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine

생성물 2

HCID 21894508Ammonium hydroxide methanolHCID 227428906-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol수율 43%

시약·촉매·용매 4

HCID 679Dimethyl Sulfoxide용매HCID 702Ethanol용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

5-[1-Methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine. A warm solution of potassium tert-butylate (2.68 g, 23.4 mmol) in tert-butanol (20 mL) was added to a room temperature solution of 1-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indole-6-carbaldehyde (5.95 g, 19.5 mmol) and 3-anilinopropionitrile (3.20 g, 21.4 mmol) in methyl sulfoxide (70 mL). After 2 h the solution was diluted with ethyl acetate, washed with water and brine, dried (MgSO4), and evaporated. This material was dissolved in ethanol (70 mL) and added to a suspension of guanidine hydrochloride (6.21 g, 64.4 mmol) in ethanol (210 mL), and the mixture was stirred at 70° C. for 22 h. Most of the solvent was distilled off, and the residue was partitioned between water and ether. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2; CH2CL2/MeOH/NH4OH 19:1:0.05) afforded the title compound (3.32 g, 43%).Yellow solid.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. dissolutionThis material was dissolved in ethanol (70 mL)
  5. distillationMost of the solvent was distilled off
  6. customthe residue was partitioned between water and ether
  7. washThe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

출처 및 근거

ORD 기록
ord-aa6521f3357140e79c9ec53c35307513
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703397B2

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