Hydrochloric Acid → 5-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine

HRID 2266089Notes

Reaction equation

HRID 2266089 reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:14])=[CH:9][N:10]2[CH3:13])=[CH:6][C:5]=1[O:15][C:16](=[CH:19]COC)[C:17]#[N:18])([CH3:3])[CH3:2].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29].C[O-].[Na+].Cl>C(O)C.C(OCC)C>[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:14])=[CH:9][N:10]2[CH3:13])=[CH:6][C:5]=1[O:15][C:16]1[C:17]([NH2:18])=[N:29][C:28]([NH2:30])=[N:27][CH:19]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 10942334Sodium MethoxideHCID 670534062-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile

Product 1

HCID 161192135-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

5-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine was prepared from 2-(6-isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile by treatment with guanidine carbonate and sodium methoxide using the procedure of step 7 of Example 2 above. This material was dissolved in 2.5 ml absolute ethanol, and 820 ml of 1 N HCl in diethyl ether was added with stirring. Diethyl ether was added slowly until small crystals formed, and the solution was then placed in a −10 C freezer for 18 hours. The solid that had formed was collected by filtration, washed with diethyl ether, and dried under vacuum at 45 C to give 171 mg. of the hydrochloride salt, Mp: 185.1° C.

Workup

  1. customformed
  2. customThe solid that had formed
  3. filtrationwas collected by filtration
  4. washwashed with diethyl ether
  5. customdried under vacuum at 45 C
  6. customto give 171 mg

Sources & evidence

ORD record
ord-12cfe47e6e7245faa892decdfd47685e
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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