4-Methoxybenzylamine → HCID 67541451, compound

HRID 2093322Notes

Reaction equation

HRID 2093322 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:5]3[S:10][CH:9]=[CH:8][C:6]=3[N:7]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 866287402-Chloro-4-(4-methyl-piperazin-1-yl)-thieno[3,2-d]pyrimidine

Product 1

HCID 67541451HCID 67541451, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 2-chloro-4-(4-methyl-piperazin-1-yl)-thieno[3,2-d]pyrimidine (0.11 g, 0.4 mmol) in pyridine (0.34 mL) in a microwave vial was added 4-methoxybenzylamine (0.55 mL, 4.2 mmol). The reaction mixture was heated to 200° C. in the microwave for 1 h, after which pyridine was removed under reduced pressure. The resultant residue was purified by FCC (2 M NH3 in MeOH/CH2Cl2) to yield (4-methoxy-benzyl)-[4-(4-methyl-piperazin-1-yl)-thieno[3,2-d]pyrimidin-2-yl]-amine. The intermediate was then dissolved in trifluoroacetic acid (2.5 mL) and heated at 60° C. for 1.5 h. After concentrating, the residue was purified by reverse-phase chromatography (acidic conditions) to afford the desired product as a TFA salt (30 mg). MS: 250.1. 1H NMR (400 MHz, CD3OD) δ ppm 8.26 (d, J=5.6 Hz, 1H), 7.30 (d, J=5.6 Hz, 1H), 4.65-4.12 (m, 4H), 3.60-3.41 (m, 4H), 2.98 (s, 3H).

Workup

  1. customafter which pyridine was removed under reduced pressure
  2. customThe resultant residue was purified by FCC (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-34365f4e17cb4123a10982015c166459
Source dataset
uspto-grants-2013_05
Patent number
US08445482B2

Reaction notes

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