Trifluoroacetic acid → 5-(4-Amino-3-methoxyphenyl)-4-chloro-7-cyclopentylpyrrolo[2,3-d]pyrimidine

HRID 251490Notes

Reaction equation

HRID 251490 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([NH:24]C(=O)OC(C)(C)C)=[C:20]([O:32][CH3:33])[CH:19]=3)=[CH:16][N:15]([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[C:11]=2[N:12]=[CH:13][N:14]=1>ClCCl>[Cl:8][C:9]1[C:10]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([O:32][CH3:33])[CH:19]=3)=[CH:16][N:15]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53777291tert-butyl N-[4-(4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

Product 1

HCID 541919345-(4-Amino-3-methoxyphenyl)-4-chloro-7-cyclopentylpyrrolo[2,3-d]pyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 ml) was added dropwise to a solution of tert-butyl N-[4-(4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (0.58 g, 1.31 mmol) in dichloromethane (20 ml) at 0° C. The ice bath was removed and the reaction mixture was stirred at room temperature for 3 h. Most of trifluoroacetic acid and dichloromethane were removed under reduced pressure. The residue was redissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated to give 4-(4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyaniline as white solids (0.45 g, 1.31 mmol): 1H NMR (DMSO-d6, 400 MHz) δ 8.61 (s, 1H), 7.78 (s, 1H), 6.97 (d, 1H), 6.85 (dd, 1H), 6.67 (d, 1H), 5.20 (m, 1H), 4.78 (broad, 2H), 3.81 (s, 3H), 2.18 (m, 2H), 1.88-2.00 (m, 4H), 1.72 (m, 2H); MH+343.

Workup

  1. customThe ice bath was removed
  2. customMost of trifluoroacetic acid and dichloromethane were removed under reduced pressure
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ce40e58b02f94edb8d4dca42281e37ed
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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