Benzylamine → n4-Benzyl-6-chloropyrimidine-4,5-diamine

HRID 278928Notes

Reaction equation

[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[NH2:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[N:4][C:3]=1[NH:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Part A. A solution of 5-amino-4,6-dichloropyrimidine (10.0 g, 61.0 mmol) and triethylamine (12.8 mL, 91.5 mmol) in ethanol (100 mL) was treated with benzylamine (7.30 mL, 67.1 mmol), and heated to 50° C. overnight. The resulting mixture was cooled, and the resulting crystalline solid was collected by filtration. The solid was triturated with hexane, refiltered and dried under vacuum. A second crop was collected from the mother liquor and purified like the first crop to afford in total 12.67 g (48.8 mmol, 80%) of 5-amino-6-benzylamino-4-chloropyrimidine. TLC RF 0.10 (30:70 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): d 7.62 (1H, s), 7.13-6.97 (5H, m), 6.61 (1H, br t, J=5 Hz), 4.43 (2H, d, J=5.5 Hz), 4.24 (2H, br s). MS (NH3-CI): m/e 238 (4), 237 (33), 236 (15), 235 (100).

Workup

temperatureThe resulting mixture was cooled
filtrationthe resulting crystalline solid was collected by filtration
customThe solid was triturated with hexane
customdried under vacuum
customA second crop was collected from the mother liquor
custompurified like the first crop

Sources & evidence

ORD record: ord-0b02ce2881464f99ae30d8d95442e397
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362180B1

Reaction notes

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