Benzyl Alcohol → 2-Amino-4-benzyloxy-thieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 1161749Notes

Reaction equation

[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O:13][C:14]([C:16]1[S:26][C:19]2[N:20]=[C:21]([NH2:25])[N:22]=[C:23](Cl)[C:18]=2[CH:17]=1)=[O:15])C>C1COCC1>[NH2:25][C:21]1[N:22]=[C:23]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:18]2[CH:17]=[C:16]([C:14]([OH:15])=[O:13])[S:26][C:19]=2[N:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a nitrogen filled flask containing sodium hydride (0.5 mmol, 60% in mineral oil) in anhydrous THF (5 ml) was added benzyl alcohol (0.5 mmol). The suspension was stirred vigorously for 10 minutes until no more gas was evolved before being transferred to a microwave reaction tube containing 2-amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.129 g, 0.5 mmol). The sealed tube was heated to 90° C. for 5 mins using 300 W in a CEM microwave apparatus (CARE!). The reaction mixture was partitioned between DCM and water, the water layer neutralised and evaporated to dryness in vacuo to leave the pure product.

Workup

custombefore being transferred to a microwave reaction tube
customThe reaction mixture was partitioned between DCM and water
customevaporated to dryness in vacuo
customto leave the pure product

Sources & evidence

ORD record: ord-2a5f81ebdf854fff976ae8f1abfafd7c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820658B2

Reaction notes

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