Ammonia → 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

HRID 567758Notes

Reaction equation

HRID 567758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15](OCC)=[O:16])[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[NH3:23]>CO>[NH2:23][C:15]([C:13]1[NH:12][C:8]2[N:9]=[CH:10][N:11]=[C:6]([NH:5][C:4]3[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[CH:3]=3)[C:7]=2[CH:14]=1)=[O:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 212626224-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 212626756-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

90 mg (0.285 mmol) of 4-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo-[2,3-d]pyrimidine (stage 1.4) in 30 ml of methanol and≈5 g of ammonia are heated at 120° C. for 48 h in an autoclave. The reaction mixture is treated with silica gel, evaporated, applied to a silica gel column as a powder and finally eluted with methylene chloride/methanol/THF (210:35:10). Filtration with methanol through an alumina column (basic) and stirring in ethyl acetate yields 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=8.1; TLC-Rf=0.18 (CH2Cl2/methanol [10:1]); high resolution MS: (M+H)+=288.0669 (calc. 288.0652).

Workup

  1. additionThe reaction mixture is treated with silica gel
  2. customevaporated
  3. washfinally eluted with methylene chloride/methanol/THF (210:35:10)
  4. filtrationFiltration with methanol through an alumina column (basic)

Sources & evidence

ORD record
ord-322b80f700a349c1b76cea190c98c2be
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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