Tert-Butylamine → 6-(N-tert.-Butyl-carbamoyl)-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369872Notes

Reaction equation

HRID 369872 reaction equation
[C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)([OH:3])=O.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].C(P(=O)(OCC)OCC)#N>CN(C=O)C>[C:21]([NH:25][C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)=[O:3])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 76257Diethyl cyanophosphonateHCID 212626746-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 232827596-(N-tert.-Butyl-carbamoyl)-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 144 mg (0.50 mmol) of 6-carboxy-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine (cf. Example 42) and 116 μl (1.1 mmol) of tert.-butylamine in 5 ml of DMF are added 114 μl (0.75 mmol) of diethyl cyanophosphonate (Aldrich; Milwaukee/USA). After 4 h, the reaction mixture is poured onto ice water, stirred for 30 min and finally filtered. The residue is redissolved in isopropanol, treated with charcoal and filtered. Concentration in vacuo and washing with dichloromethane/diethyl ether yields the title compound; HPLC: tRet (Grad20)=11.4; FAB-MS: (M+H)+ =344.

Workup

  1. additionthe reaction mixture is poured onto ice water
  2. filtrationfinally filtered
  3. dissolutionThe residue is redissolved in isopropanol
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. concentrationConcentration in vacuo
  7. washwashing with dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-015f9b952a0447c4ac4918724c83e99a
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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