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

HRID 48457

反応式

HRID 48457 の反応式
[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

参加物

11

反応物 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

生成物 2

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

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 702Ethanol溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aa6521f3357140e79c9ec53c35307513
出典データセット
uspto-grants-2004_03
特許番号
US06703397B2

関連ノート

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