Water → 6-[4-[3-[4-(1-Adamantyl)-1-piperazinyl]-2-hydroxypropoxy]phenyl]-2,4,7-triaminopteridine

HRID 1768949Notes

Reaction equation

[C:1]12([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([OH:30])[CH2:19][O:20][C:21]4[CH:29]=[CH:28][C:24]([CH2:25][C:26]#[N:27])=[CH:23][CH:22]=4)[CH2:13][CH2:12]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[N:31]([C:33]1[C:34]([NH2:41])=[N:35][C:36]([NH2:40])=[N:37][C:38]=1[NH2:39])=O.C(OCC[O-])C.[Na+].O>C(OCCO)C>[C:1]12([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([OH:30])[CH2:19][O:20][C:21]4[CH:22]=[CH:23][C:24]([C:25]5[N:31]=[C:33]6[C:34](=[N:41][C:26]=5[NH2:27])[N:35]=[C:36]([NH2:40])[N:37]=[C:38]6[NH2:39])=[CH:28][CH:29]=4)[CH2:13][CH2:12]3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-[3-[4-(1-adamantyl)-1-piperazinyl]-2-hydroxypropoxy]benzylcyanide (3.44 g, 8.4 mmol), 5-nitroso-2,4,6-triamino-pyrimidine (1.08 g, 7.0 mmol) and 0.2N sodium-(2-ethoxyethoxide) in 2-ethoxyethanol (35 ml) was stirred at 120° C. for 30 minutes. After cooling to about 90° C. 100 ml of water was added and the mixture was cooled to room temperature followed by stirring in an ice-water bath for 30 minutes. The precipitate was collected, washed with water and acetonitrile to give the title compound (3.23 g) as a yellow powder, mp. 287°-289° C. (dec.), yield: 84.6%.

Workup

temperatureAfter cooling to about 90° C
temperaturethe mixture was cooled to room temperature
stirringby stirring in an ice-water bath for 30 minutes
customThe precipitate was collected
washwashed with water and acetonitrile

Sources & evidence

ORD record: ord-1562907737314174bb5ffe0ae7b8eab7
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380724

Reaction notes

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