Water → (2R)-2-{[2-Amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino}pentan-1-ol

HRID 550748Notes

Reaction equation

[CH2:1]([S:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][C:16]([NH2:18])=[N:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:29][C@H:30]([CH2:33][CH2:34][CH3:35])[CH2:31][OH:32].O>CN1C(=O)CCC1>[NH2:18][C:16]1[S:17][C:12]2[C:11]([NH:29][C@H:30]([CH2:33][CH2:34][CH3:35])[CH2:31][OH:32])=[N:10][C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][C:13]=2[N:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine (6.0 g, 19.4 mmol) was dissolved in NMP (30 mL). DIPEA (8.4 mL, 48.5 mmol) and 2-amino-(2R)-1-pentanol (3.5 g, 33.9 mmol) were added and the mixture was heated to 110° C. for 4 days. After cooling to ambient temperature, the mixture was poured into water (200 mL). The precipitated product was collected by filtration, washed with water and used in the next step without further purification (7.0 g, 97% yield).

Workup

temperatureAfter cooling to ambient temperature
filtrationThe precipitated product was collected by filtration
washwashed with water
customused in the next step without further purification (7.0 g, 97% yield)

Sources & evidence

ORD record: ord-ed3de670a57a443e9c9ea86ab21ac2f2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947693B2

Reaction notes

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