Water → HCID 54101464, compound

HRID 369870Notes

Reaction equation

HRID 369870 reaction equation
C(O[C:4]([C:6]1[NH:23][C:9]2[N:10]=[CH:11][N:12]=[C:13]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:8]=2[CH:7]=1)=[O:5])C.[C-:24]#[N:25].[Na+].O>CN.C1COCC1>[CH3:24][NH:25][C:4]([C:6]1[NH:23][C:9]2[N:10]=[CH:11][N:12]=[C:13]([NH:14][C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:8]=2[CH:7]=1)=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 20637716HCID 20637716, compound

Product 1

HCID 54101464HCID 54101464, compound

Reagents, catalysts & solvents 2

HCID 6329MethylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a bomb tube, 155 mg (0.50 mmol) of 6-ethoxycarbonyl-4-[1(R)-phenyl-ethylamino]-7H-pyrrolo[2,3-d]pyrimidine and 2.5 mg (0.05 mmol) of NaCN in 4 ml of methylamine (33% in ethanol) are heated at 50° C. for 30 hours. The reaction mixture is dissolved in THF, 25 ml of water are added thereto and concentration by evaporation is carried out to a residual volume of =25 ml. The resulting crystals are filtered off and washed with water. Recrystallization from hot THF and ethyl acetate yields the title compound; HPLC: tRet (Grad20)=8.3; TLC-Rf =0.31 (CH2Cl2 /methanol [10:1]); FAB-MS: (M+H)+ =296.

Workup

  1. concentrationconcentration
  2. customby evaporation
  3. filtrationThe resulting crystals are filtered off
  4. washwashed with water
  5. customRecrystallization from hot THF and ethyl acetate

Sources & evidence

ORD record
ord-fd8befb2293847678577d9644014c703
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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