Water → phenyl[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]-amine

HRID 2067706Notes

Reaction equation

HRID 2067706 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:9]#[C:10][C:11]([C:13]1[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[N:15](C(OC(C)(C)C)=O)[CH:14]=1)=O.C(=O)(O)O.[C:35]1([NH:41][C:42]([NH2:44])=[NH:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>COCCO>[C:35]1([NH:41][C:42]2[N:44]=[C:11]([C:13]3[C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:16]=4[NH:15][CH:14]=3)[CH:10]=[CH:9][N:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16217093Carbonic acid, compound with phenylguanidine (1:1)HCID 58230463Tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 24884486phenyl[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
40 °C

Procedure

1.2 104 mg (0.75 mmol) of potassium carbonate are added to a solution of 103 mg (0.30 mmol of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate and 148 mg (0.75 mmol) of phenylguanidine carbonate in 1.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 68 hours. After cooling, 10 ml of water are added, and the mixture is stirred at 40° C. for 1 h. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving phenyl-[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]amine (“A1”) as pale-brown solid; ESI 287;

Workup

  1. temperaturethe mixture is heated at the boil for 68 hours
  2. temperatureAfter cooling
  3. customThe precipitate formed
  4. filtrationis filtered off with suction
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0ca1724f31414102b60586fa4f270013
Source dataset
uspto-grants-2012_10
Patent number
US08293891B2

Reaction notes

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