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

HRID 48457
Notes
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Reaction equation

HRID 48457 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 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

Product 2

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

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aa6521f3357140e79c9ec53c35307513
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06703397B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes