Trifluoroacetic acid → 2-Chloro-6-(hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2066550Notes

Reaction equation

HRID 2066550 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12]([CH2:16][C:17]3[S:25][C:24]4[C:23]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[N:22][C:21]([Cl:32])=[N:20][C:19]=4[CH:18]=3)[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:32][C:21]1[N:22]=[C:23]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[C:24]2[S:25][C:17]([CH2:16][N:12]3[CH2:13][CH:14]4[CH:10]([CH2:9][NH:8][CH2:15]4)[CH2:11]3)=[CH:18][C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 581170715-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

Product 1

HCID 866501872-Chloro-6-(hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidineYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (390 mg; 0.81 mmol) in CH2Cl2 (4 mL) was added TFA (6 mL). The reaction mixture was stirred at RT for 4 h upon which time volatiles were removed in vacuo. Purification by SCX-2 gave the title compound as an off-white solid (273 mg; 89%).

Workup

  1. customwere removed in vacuo
  2. customPurification by SCX-2

Sources & evidence

ORD record
ord-c4403a948d3c40e196298d4e59bda198
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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