Hydrochloric Acid → HCID 22736336, compound

HRID 51565Notes

Reaction equation

HRID 51565 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([CH:19]3[CH2:28][CH2:27][C:22]4(OCC[O:23]4)[CH2:21][CH2:20]3)[CH:10]=2)=[CH:5][C:4]=1[F:29].CO>CC(C)=O.C(Cl)Cl>[NH2:18][C:16]1[C:17]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([NH2:2])=[C:4]([F:29])[CH:5]=3)=[CH:10][N:11]([CH:19]3[CH2:20][CH2:21][C:22](=[O:23])[CH2:27][CH2:28]3)[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 227362115-(4-amino-3-fluorophenyl)-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 22736336HCID 22736336, compoundYield 77,328,568%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

5M HCl (300 mL) was added slowly to a solution of 5-(4-amino-3-fluorophenyl)-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (18.49 g, 48.28 nmol) in acetone (800 mL) at 0° C. the resulting dark orange-brown solution was heated at 60° C. for 4 h. (t.l.c. analysis using 10% MeOH in CH2Cl2). The acetone was removed under reduced pressure and the acidic layer was basified to approx. pH 8 using sat. aq. Na2CO3. The resulting precipitate was collect by filtration and scrupulously dried to afford 4-[4-amino-5-(4-amino-3-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclohexanone as a light brown solid (12.67 g, 77%). A second crop was also obtained from the mother liquor on standing (2.01 g, 12%), 1H NMR (400 MHz, d6-DMSO) 2.27(2H, m), 2.30 (4H, br d), 2.73(2H, m), 5.14(1H, m), 5.20(2H, brs), 6.05(2H, brs), 6.85 (1H, t), 6.97(1H, dd), 7.06(1H, dd), 7.35(1H, s) and 8.12(1H, s) and m/z 340.1(MH+).

Workup

  1. customThe acetone was removed under reduced pressure
  2. filtrationThe resulting precipitate was collect by filtration
  3. customscrupulously dried

Sources & evidence

ORD record
ord-d0251cb2acfd4806b3d1397c036b0785
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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